Triethylamine → 2'-(3,4,5-Trimethoxybenzoyl)spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:3][NH:2]1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38])[C:31](Cl)=[O:32]>ClCCl>[CH3:40][O:39][C:35]1[CH:34]=[C:30]([CH:29]=[C:28]([O:27][CH3:26])[C:36]=1[O:37][CH3:38])[C:31]([N:2]1[CH2:3][C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cold solution of spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (8.0 g) and triethylamine (4.0 g) in dry dichloromethane (100 ml) is added dropwise a solution of 3,4,5-trimethoxybenzoyl chloride (9.5 g) in dry dichloromethane (50 ml). After stirring at ambient temperature for 24 hours, the mixture is washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is evaporated to an oil, which solidifies upon trituration with hexanes. The solid is recrystallized twice from hexane/methanol to yield 10.0 g (66%) of product, mp 122° (dec.).
Workup
- washthe mixture is washed with water (2x), saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtering
- customthe solvent is evaporated to an oil, which
- customThe solid is recrystallized twice from hexane/methanol
Sources & evidence
- ORD record
- ord-4ad45b24b9694b079a1c03223c707a2d
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04374137
Reaction notes
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