1-(3-methoxy-2-nitrophenyl)-1,3-hexanedione -Drug Synthesis Database

【结构式】

【分子编号】32774

【品名】1-(3-methoxy-2-nitrophenyl)-1,3-hexanedione

【CA登记号】

【分子式】C₁₃H₁₅NO₅

【分子量】265.26584

【元素组成】C 58.86% H 5.7% N 5.28% O 30.16%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

The reaction of 3-methoxy-2-nitrobenzoic acid methyl ester (I) with 2-pentanone (II) by means of LDA gives 1-(3-methoxy-2-nitrophenyl)hexane-1,3-dione (III), which is condensed with dimethylformamide dimethyl acetal (DMFA) yielding the enamine (IV). The cyclization of (IV) by hydrogenation with H2 over Pd/C affords quinolone (V), which is treated with refluxing POCl3 to give 1-(4-chloro-8-methoxyquinolin-3-yl)-1-butanone (VI). Finally, this compound is condensed with o-toluidine in refluxing dioxane. The intermediate, the quinolone (V) has also been obtained as follows: The reaction of 1-chloro-1-hexen-3-one (VIII) with NaOH in methanol gives 3-oxohexanal (IX) (enol form), which is condensed with 2-amino-3-methoxybenzoic acid methyl ester (X) yielding the enamine (XI). Finally, this compound is cyclized by means of sodium methoxide to afford the desired quinolone (V).

参考文献中间体

合成目标

【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
(I)	32773	methyl 3-methoxy-2-nitrobenzoate	5307-17-5	C₉H₉NO₅	详情	详情
(II)	15048	2-pentanone	107-87-9	C₅H₁₀O	详情	详情
(III)	32774	1-(3-methoxy-2-nitrophenyl)-1,3-hexanedione		C₁₃H₁₅NO₅	详情	详情
(IV)	32775	2-[(E)-(dimethylamino)methylidene]-1-(3-methoxy-2-nitrophenyl)-1,3-hexanedione		C₁₆H₂₀N₂O₅	详情	详情
(V)	12519	3-Butyryl-8-methoxy-4(1H)-quinolinone		C₁₄H₁₅NO₃	详情	详情
(VI)	12520	1-(4-Chloro-8-methoxy-3-quinolinyl)-1-butanone		C₁₄H₁₄ClNO₂	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
(VIII)	32776	(Z)-1-chloro-1-hexen-3-one		C₆H₉ClO	详情	详情
(IX)	32777	(Z)-1-hydroxy-1-hexen-3-one		C₆H₁₀O₂	详情	详情
(X)	32778	methyl 2-amino-3-methoxybenzoate		C₉H₁₁NO₃	详情	详情
(XI)	32779	methyl 3-methoxy-2-[[(Z)-3-oxo-1-hexenyl]amino]benzoate		C₁₅H₁₉NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XV)

The intermediate quinolone (V) has also been obtained by two other ways: a) The reaction of 3-methoxy-2-nitrobenzoic acid methyl ester (XIII) with 2-pentanone (XIV) by means of LDA gives 1-(3-methoxy-2-nitrophenyl)hexane-1,3-dione (XV), which is condensed with dimethylformamide dimethyl acetal (DMFA) yielding the enamine (XVI). Finally, this compound is cyclized by hydrogenation with H2 over Pd/C to afford the desired quinolone (V). b) The reaction of 1-chloro-1-hexen-3-one (XVII) with NaOH in methanol gives 3-oxohexanal (XVIII) (enol form), which is condensed with 2-amino-3-methoxybenzoic acid methyl ester (XIX) yielding the enamine (XX). Finally, this compound is cyclized by means of sodium methoxide to afford the desired quinolone (V).

参考文献中间体

合成目标

【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
(V)	12519	3-Butyryl-8-methoxy-4(1H)-quinolinone		C₁₄H₁₅NO₃	详情	详情
(XIII)	32773	methyl 3-methoxy-2-nitrobenzoate	5307-17-5	C₉H₉NO₅	详情	详情
(XIV)	15048	2-pentanone	107-87-9	C₅H₁₀O	详情	详情
(XV)	32774	1-(3-methoxy-2-nitrophenyl)-1,3-hexanedione		C₁₃H₁₅NO₅	详情	详情
(XVI)	32775	2-[(E)-(dimethylamino)methylidene]-1-(3-methoxy-2-nitrophenyl)-1,3-hexanedione		C₁₆H₂₀N₂O₅	详情	详情
(XVII)	32776	(Z)-1-chloro-1-hexen-3-one		C₆H₉ClO	详情	详情
(XVIII)	32777	(Z)-1-hydroxy-1-hexen-3-one		C₆H₁₀O₂	详情	详情
(XIX)	32778	methyl 2-amino-3-methoxybenzoate		C₉H₁₁NO₃	详情	详情
(XX)	32779	methyl 3-methoxy-2-[[(Z)-3-oxo-1-hexenyl]amino]benzoate		C₁₅H₁₉NO₄	详情	详情

Extended Information