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

HRID 370642Notes

Reaction equation

HRID 370642 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=O.[CH3:15][N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:15][N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][C:20]([CH:1]([C:3]2[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][CH:4]=2)[C:3]2[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 147939725-(Dimethylamino)-2-formylbenzoic acid

Product 1

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

Procedure

In another known process for the preparation of CVL there are three steps. The first step comprises the interaction of the methyl ester of 2-formyl-5-dimethylaminobenzoic acid with two equivalents of N,N-dimethylaniline to obtain the methyl ester of 2-[bis(4-dimethylaminophenyl)methyl]-5-dimethylaminobenzoic acid. After isolation, this benzoic acid is oxidized in the second step and finally in the third step the oxidized product is saponified and the lactone ring is closed to obtain the 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide (CVL).

Workup

  1. customIn another known process for the preparation of CVL there

Sources & evidence

ORD record
ord-af9299be328f4ffbab66c2edb49f4adf
Source dataset
uspto-grants-1985_07
Patent number
US04528136

Reaction notes

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