1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine -Drug Synthesis Database

【结构式】

【分子编号】53911

【品名】1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine

【CA登记号】618-40-6

【分子式】C₇H₁₀N₂

【分子量】122.16988

【元素组成】C 68.82% H 8.25% N 22.93%

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：(VI)

Treatment of 3-methoxy-2-cyclohexen-1-one (I) with n-butyllithium and diisopropylamine in THF, followed by addition of N,N-dimethylmethylene ammonium iodide (Eschenmoser's salt) (II) and precipitation with maleic acid, furnishes maleate (III). Methylation of (III) with iodomethane in DMF, followed by condensation with 2-methylimidazole (IV), affords compound (V), which is then converted into methylphenyl hydrazino derivative (VII) by first treatment with HCl in H2O followed by reaction with 1-methyl-1-phenylhydrazine (VI). Cyclization of (VII) is then performed by means of ZnCl2 in HOAc at 85 C to give carbazolone (VIII), and finally the target product is obtained by formation of the hydrochloride dihydrate salt.

参考文献中间体

合成目标

【1】 Bell, J.A.; Ewan, G.B.; Oxford, A.W.; Humber, D.C.; Eldred, C.D.; Costes, I.H. (GlaxoSmithKline plc); Process for the preparation of 3-imidazolylmethyltetrahydrocarbazolones. EP 0219929 .

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)	53908	3-Methoxy-2-cyclohexen-1-one	16807-60-6	C₇H₁₀O₂	详情	详情
(II)	48555	Eschenmoser's salt; N,N-Dimethylmethyleneimmonium chloride; N,N-Dimethylmethyleneimmonium iodide		C₃H₈IN	详情	详情
(III)	55373			C₁₄H₂₁NO₆	详情	详情
(IV)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(V)	53910	3-methoxy-6-[(2-methyl-1H-imidazol-1-yl)methyl]-2-cyclohexen-1-one		C₁₂H₁₆N₂O₂	详情	详情
(VI)	53911	1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine	618-40-6	C₇H₁₀N₂	详情	详情
(VII)	53912	6-[(2-methyl-1H-imidazol-1-yl)methyl]-3-(2-methyl-2-phenylhydrazino)-2-cyclohexen-1-one	n/a	C₁₈H₂₂N₄O	详情	详情
(VIII)	53903	9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one	n/a	C₁₈H₁₉N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：

2) Alkylation of the tetrahydropyridoindolone (VII) with 5-chloromethyl-4-methyloxazole (VIII) in dimethoxyethane in the presence of sodium hydride affords (IX). Ammonolysis of this material is carried out by heating with formamide.

参考文献中间体

合成目标

【1】 Oxford, A.W.; Hagan, R.M.; Tyers, M.B.; Kilpatrick, G.J.; North, P.C.; GR-68755 Hydrochloride. Drugs Fut 1992, 17, 8, 660.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	53911	1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine	618-40-6	C₇H₁₀N₂	详情	详情
(V)	15737	dihydro-2,4(1H,3H)-pyridinedione		C₅H₇NO₂	详情	详情
(VI)	15738	4-[(Z)-methyl(phenyl)-lambda(5)-azanylidene]dihydro-2(1H,3H)-pyridinone		C₁₂H₁₆N₂O	详情	详情
(VII)	15739	5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one		C₁₂H₁₂N₂O	详情	详情
(VIII)	15740	5-(chloromethyl)-4-methyl-1,3-oxazole		C₅H₆ClNO	详情	详情
(IX)	15741	5-methyl-2-[(4-methyl-1,3-oxazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one		C₁₇H₁₇N₃O₂	详情	详情

Extended Information