3,4-dihydro-1H-isochromene -Drug Synthesis Database

【结构式】

【分子编号】34866

【品名】3,4-dihydro-1H-isochromene

【CA登记号】493-05-0

【分子式】C₉H₁₀O

【分子量】134.1778

【元素组成】C 80.56% H 7.51% O 11.92%

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：(VII)

The bromination of 3,4-dihydro-1H-2-benzopyran (VII) with Br2 gives the 1-bromo derivative (VIII), which, without isolation, is treated with hot HBr yielding 2-(2-bromoethyl)benzaldehyde (IX). The condensation of (IX) with nitromethane in acidic medium affords the nitrostyrene (X), which is cyclized with treatment with FeCl3 and acetyl chloride giving 4-(2-bromoethyl)-3-chloroindolin-2-one (XI). The dechlorination of (XI) with NaH2PO2 over Pd/C yields 4-(2-bromoethyl)indolin-2-one (XII), which is finally condensed with dipropylamine (II).

参考文献中间体

合成目标

【1】 Hayler, J.D.; et al.; Development of large-scale syntheses or ropinirole in the pursuit of a manufacturing process. Org Process Res Dev 1998, 2, 1, 3.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
	39563	nitromethane	75-52-5	CH₃NO₂	详情	详情
(II)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情
(VII)	34866	3,4-dihydro-1H-isochromene	493-05-0	C₉H₁₀O	详情	详情
(VIII)	34867	1-bromo-3,4-dihydro-1H-isochromene		C₉H₉BrO	详情	详情
(IX)	34868	2-(2-bromoethyl)benzaldehyde		C₉H₉BrO	详情	详情
(X)	34869	1-(2-bromoethyl)-2-[(E)-2-nitroethenyl]benzene		C₁₀H₁₀BrNO₂	详情	详情
(XI)	34870	4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one		C₁₀H₉BrClNO	详情	详情
(XII)	34871	4-(2-bromoethyl)-1,3-dihydro-2H-indol-2-one		C₁₀H₁₀BrNO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

The reaction of 3,4-dihydro-1H-2-benzopyran (VII) with benzoyl chloride and ZnCl2 gives benzoic acid 2-[2-(chloromethyl)phenyl]ethyl ester (XIII), which is condensed with hexamethylenetetramine (XIV) yielding the amminium salt (XV). The hydrolysis of (XV) affords 2-(2-benzoyloxyethyl) benzaldehyde (XVI), which is condensed with nitromethane as before to give the nitrostyrene (XVII). The cyclization of (XVII) with FeCl3 and acetyl chloride as before yields 4-(2-benzoyloxyethyl)-3-chloroindolin-2-one (XVIII), which is dechlorinated with hydrazine and Pd/C to the indolinone (XIX). The hydrolysis of (XIX) with NaOH affords 4-(2-hydroxyethyl)indolin-2-one (XX), which is acylated with TsCl giving the tosylate (XXI). Finally, this compound is condensed with dipropylamine (II).

参考文献中间体

合成目标

【1】 Hayler, J.D.; et al.; Development of large-scale syntheses or ropinirole in the pursuit of a manufacturing process. Org Process Res Dev 1998, 2, 1, 3.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
	39563	nitromethane	75-52-5	CH₃NO₂	详情	详情
(II)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情
(VII)	34866	3,4-dihydro-1H-isochromene	493-05-0	C₉H₁₀O	详情	详情
(XIII)	34872	2-(chloromethyl)phenethyl benzoate		C₁₆H₁₅ClO₂	详情	详情
(XIV)	34873	1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane	100-97-0	C₆H₁₂N₄	详情	详情
(XV)	34874	1-[2-[2-(benzoyloxy)ethyl]benzyl]-3,5,7-triaza-1-azoniatricyclo[3.3.1.1(3,7)]decane chloride		C₂₂H₂₇ClN₄O₂	详情	详情
(XVI)	34875	2-formylphenethyl benzoate		C₁₆H₁₄O₃	详情	详情
(XVII)	34876	2-[(E)-2-nitroethenyl]phenethyl benzoate		C₁₇H₁₅NO₄	详情	详情
(XVIII)	34877	2-(3-chloro-2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl benzoate		C₁₇H₁₄ClNO₃	详情	详情
(XIX)	34878	2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl benzoate		C₁₇H₁₅NO₃	详情	详情
(XX)	34879	4-(2-Hydroxyethyl)indolin-2-one	139122-19-3	C₁₀H₁₁NO₂	详情	详情
(XXI)	34880	4-heptanol	589-55-9	C₇H₁₆O	详情	详情

Extended Information