N,N-Dimethylaniline → 2-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

HRID 370641Notes

Reaction equation

HRID 370641 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[CH:5][CH:4]=1.[CH3:23][N:24]([CH3:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:28]2[CH:29]=[CH:30][C:25]([N:24]([CH3:31])[CH3:23])=[CH:26][CH:27]=2)[C:18]2[CH:17]=[CH:16][C:15]([N:19]([CH3:21])[CH3:20])=[CH:14][C:13]=2[C:11]([OH:10])=[O:12])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-

Product 1

HCID 1020632-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

Procedure

In a second synthetic route to CVL, which is also a multi-step synthesis, 4-dimethylaminobenzaldehyde is reacted with 3-dimethylaminobenzoic acid to obtain 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide in the first step. In a second step, the 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide from step one is interacted with N,N-dimethylaniline in the presence of a Friedel-Crafts type catalyst to obtain 2-[bis(4-dimethylaminophenyl)methyl]-5-dimethylaminobenzoic acid. In a third step, the benzoic acid from step two is oxidized to obtain 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide.

Sources & evidence

ORD record
ord-98487d7453524986b3b58127282471d0
Source dataset
uspto-grants-1985_07
Patent number
US04528136

Reaction notes

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