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

HRID 1982295Notes

Reaction equation

HRID 1982295 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][N:6]([CH3:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:14][N:15]([CH3:35])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[C:31]3[C:26](=[CH:27][C:28]([N:32]([CH3:34])[CH3:33])=[CH:29][CH:30]=3)[C:24](=[O:25])[O:23]2)=[CH:18][CH:17]=1>[Cl-].[Zn+2].[Cl-]>[CH3:5][N:6]([CH3:13])[C:7]1[CH:12]=[CH:11][C:10]([CH:22]([C:31]2[CH:30]=[CH:29][C:28]([N:32]([CH3:33])[CH3:34])=[CH:27][C:26]=2[C:24]([OH:25])=[O:23])[C:19]2[CH:18]=[CH:17][C:16]([N:15]([CH3:14])[CH3:35])=[CH:21][CH:20]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-HCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Proceeding in a manner similar to that described in part A above, but replacing the anhydrous zinc chloride with 9.3 g of anhydrous aluminum chloride, 70.0 ml of N,N-dimethylaniline and 14.9 g of 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide, prepared as described in Example 1, part A above were interacted to obtain 16.1 g of 2-[4,4'-bis(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid, a light blue powder which melted at 209°-213° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-94e42cf5dd5344908659417591ba8fa9
Source dataset
uspto-grants-1986_06
Patent number
US04595768

Reaction notes

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