N-bromobutanimide → 2-Bromomethyl-4-(3,4-dimethoxyphenyl)-3-isovaleryl-6,7-dimethoxyquinoline

HRID 1684580Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[C:13]([CH3:25])[C:12]=2[C:26](=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Br:32]N1C(=O)CCC1=O>>[Br:32][CH2:25][C:13]1[C:12]([C:26](=[O:31])[CH2:27][CH:28]([CH3:29])[CH3:30])=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=1

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 190399034-(3,4-Dimethoxyphenyl)-3-isovaleryl-6,7-dimethoxy-2-methylquinoline

Product 1

HCID 190399002-Bromomethyl-4-(3,4-dimethoxyphenyl)-3-isovaleryl-6,7-dimethoxyquinoline

Procedure

According to the same manner as that described in Reference Example 5, 4-(3,4-dimethoxyphenyl)-3-isovaleryl-6,7-dimethoxy-2-methylquinoline was brominated with N-bromo-succinimide (NBS) to give 2-bromomethyl-4-(3,4-dimethoxyphenyl)-3-isovaleryl-6,7-dimethoxyquinoline. This compound was recrystallized from ethyl acetate - hexane to give colorless prisms. mp. 159°-161° C.

Sources & evidence

ORD record: ord-5cb2dcb6702342eea5ca762fe29fe998
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05641788

Reaction notes

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