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【结 构 式】

【分子编号】32790

【品名】Chloro(propyl)magnesium

【CA登记号】2234-82-4

【 分 子 式 】C3H7ClMg

【 分 子 量 】102.84628

【元素组成】C 35.04% H 6.86% Cl 34.47% Mg 23.63%

与该中间体有关的原料药合成路线共 6 条

合成路线1

该中间体在本合成路线中的序号:(XXIV)

The condensation of ethoxymethylenemalonic acid diethyl ester (XVI) with 2-methoxyaniline (XVII) in hot toluene gives the aminomethylene derivative (XVIII), which is cyclized with POCl3 and polyphosphoric acid (PPA) at 100 C yielding 8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (XIX), which is hydrolyzed with NaOH in methanol to the corresponding free acid (XX), and treated with refluxing SOCl2 to afford 4-chloro-8-methoxyquinoline-3-carbonyl chloride (XXI). The reaction of (XXI) with dimethylamine gives the corresponding amide (XXII), which is condensed with o-toluidine (VII) in refluxing dioxane yielding the expected secondary amine (XXIII). Finally, this compound is treated with propylmagnesium chloride (XXIV) to afford the target compound.

1 Atkins, R.J.; et al.; Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amini]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quin. Org Process Res Dev 1997, 1, 3, 185.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
19443 N-methylmethanamine; N,N-dimethylamine 124-40-3 C2H7N 详情 详情
40593 Sulfurous oxychloride; Thionyl chloride 7719-09-7 Cl2OS 详情 详情
(VII) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(XVI) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(XVII) 25193 2-methoxyphenylamine; 2-methoxyaniline 517-28-2 C7H9NO 详情 详情
(XVIII) 32784 diethyl 2-[(2-methoxyanilino)methylene]malonate C15H19NO5 详情 详情
(XIX) 32785 ethyl 8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate C13H13NO4 详情 详情
(XX) 32786 8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C11H9NO4 详情 详情
(XXI) 32787 4-chloro-8-methoxy-3-quinolinecarbonyl chloride C11H7Cl2NO2 详情 详情
(XXII) 32788 4-chloro-8-methoxy-N,N-dimethyl-3-quinolinecarboxamide C13H13ClN2O2 详情 详情
(XXIII) 32789 8-methoxy-N,N-dimethyl-4-(2-toluidino)-3-quinolinecarboxamide C20H21N3O2 详情 详情
(XXIV) 32790 Chloro(propyl)magnesium 2234-82-4 C3H7ClMg 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XXIV)

The reaction of acyl chloride (XXI) with propylmagnesium chloride (XXIV) gives 1-(4-chloro-8-methoxyquinolin-3-yl)-1-butanone (XXV), which is finally condensed with o-toluidine (VII) in refluxing dioxane to afford the target compound.

1 Atkins, R.J.; et al.; Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amini]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quin. Org Process Res Dev 1997, 1, 3, 185.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(XXI) 32787 4-chloro-8-methoxy-3-quinolinecarbonyl chloride C11H7Cl2NO2 详情 详情
(XXIV) 32790 Chloro(propyl)magnesium 2234-82-4 C3H7ClMg 详情 详情
(XXV) 12520 1-(4-Chloro-8-methoxy-3-quinolinyl)-1-butanone C14H14ClNO2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(XXIV)

The cyclization of (XVIII) in refluxing POCl3 gives 4-chloro-8-methoxyquinoline-3-carboxylic acid ethyl ester (XXVI), which is condensed with o-toluidine (VII) in refluxing dioxane yielding the secondary amine (XXVII). Finally, this compound is condensed with propylmagnesium chloride (XXIV) to afford the target compound.

1 Atkins, R.J.; et al.; Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amini]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quin. Org Process Res Dev 1997, 1, 3, 185.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(XVIII) 32784 diethyl 2-[(2-methoxyanilino)methylene]malonate C15H19NO5 详情 详情
(XXIV) 32790 Chloro(propyl)magnesium 2234-82-4 C3H7ClMg 详情 详情
(XXVI) 32791 ethyl 4-chloro-8-methoxy-3-quinolinecarboxylate C13H12ClNO3 详情 详情
(XXVII) 32792 ethyl 8-methoxy-4-(2-toluidino)-3-quinolinecarboxylate C20H20N2O3 详情 详情

合成路线4

该中间体在本合成路线中的序号:(XXXIII)

The condensation of ethoxymethylenemalonic acid diethyl ester (XXV) with 2-methoxyaniline (XXVI) in hot toluene gives the aminomethylene derivative (XXVII), which is cyclized with POCl3 and polyphosphoric acid (PPA) at 100 C yielding 8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (XXVIII), which is hydrolyzed with NaOH in methanol to the corresponding free acid (XXIX), and treated with refluxing SOCl2 to afford 4-chloro-8-methoxyquinoline-3-carbonyl chloride (XXX). The reaction of (XXX) with dimethylamine gives the corresponding amide (XXXI), which is condensed with o-toluidine (VIII) in refluxing dioxane yielding the expected secondary amine (XXXII). Finally, this compound is treated with propylmagnesium chloride (XXXIII) to afford the intermediate (XII).

1 Atkins, R.J.; et al.; Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amini]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quin. Org Process Res Dev 1997, 1, 3, 185.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
19443 N-methylmethanamine; N,N-dimethylamine 124-40-3 C2H7N 详情 详情
40593 Sulfurous oxychloride; Thionyl chloride 7719-09-7 Cl2OS 详情 详情
(VIII) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(XII) 32799 1-[8-methoxy-4-(2-toluidino)-3-quinolinyl]-1-butanone C21H22N2O2 详情 详情
(XXV) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(XXVI) 25193 2-methoxyphenylamine; 2-methoxyaniline 517-28-2 C7H9NO 详情 详情
(XXVII) 32784 diethyl 2-[(2-methoxyanilino)methylene]malonate C15H19NO5 详情 详情
(XXVIII) 32785 ethyl 8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate C13H13NO4 详情 详情
(XXIX) 32786 8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C11H9NO4 详情 详情
(XXX) 32787 4-chloro-8-methoxy-3-quinolinecarbonyl chloride C11H7Cl2NO2 详情 详情
(XXXI) 32788 4-chloro-8-methoxy-N,N-dimethyl-3-quinolinecarboxamide C13H13ClN2O2 详情 详情
(XXXII) 32789 8-methoxy-N,N-dimethyl-4-(2-toluidino)-3-quinolinecarboxamide C20H21N3O2 详情 详情
(XXXIII) 32790 Chloro(propyl)magnesium 2234-82-4 C3H7ClMg 详情 详情

合成路线5

该中间体在本合成路线中的序号:(XXXIII)

The reaction of acyl chloride (XXX) with propylmagnesium chloride (XXXIII) gives 1-(4-chloro-8-methoxyquinolin-3-yl)-1-butanone (XXXIV), which is finally condensed with o-toluidine (VIII) in refluxing dioxane to afford the intermediate (XII).

1 Atkins, R.J.; et al.; Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amini]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quin. Org Process Res Dev 1997, 1, 3, 185.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(XII) 32799 1-[8-methoxy-4-(2-toluidino)-3-quinolinyl]-1-butanone C21H22N2O2 详情 详情
(XXX) 32787 4-chloro-8-methoxy-3-quinolinecarbonyl chloride C11H7Cl2NO2 详情 详情
(XXXIII) 32790 Chloro(propyl)magnesium 2234-82-4 C3H7ClMg 详情 详情
(XXXIV) 12520 1-(4-Chloro-8-methoxy-3-quinolinyl)-1-butanone C14H14ClNO2 详情 详情

合成路线6

该中间体在本合成路线中的序号:(XXXIII)

The cyclization of (XXVII) in refluxing POCl3 gives 4-chloro-8-methoxyquinoline-3-carboxylic acid ethyl ester (XXXV), which is condensed with o-toluidine (VIII) in refluxing dioxane yielding the secondary amine (XXXVI). Finally, this compound is condensed with propylmagnesium chloride (XXXIII) to afford the intermediate (XII).

1 Atkins, R.J.; et al.; Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amini]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quin. Org Process Res Dev 1997, 1, 3, 185.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(XII) 32799 1-[8-methoxy-4-(2-toluidino)-3-quinolinyl]-1-butanone C21H22N2O2 详情 详情
(XXVII) 32784 diethyl 2-[(2-methoxyanilino)methylene]malonate C15H19NO5 详情 详情
(XXXIII) 32790 Chloro(propyl)magnesium 2234-82-4 C3H7ClMg 详情 详情
(XXXV) 32791 ethyl 4-chloro-8-methoxy-3-quinolinecarboxylate C13H12ClNO3 详情 详情
(XXXVI) 32792 ethyl 8-methoxy-4-(2-toluidino)-3-quinolinecarboxylate C20H20N2O3 详情 详情
Extended Information