N,N-Dimethylaniline → 6-Chloro-2[[4-(dimethylamino)phenyl]amino]3-nitrobenzoic acid

HRID 280261

Reaction equation

HRID 280261 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CN(C)C1C=CC=CC=1.Cl[C:21]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[C:26]([Cl:33])[C:22]=1[C:23]([OH:25])=[O:24]>ClCCl>[Cl:33][C:26]1[C:22]([C:23]([OH:25])=[O:24])=[C:21]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][CH:5]=2)[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 7472N,N-dimethyl-p-phenylenediamineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 135883486-Chloro-2[[4-(dimethylamino)phenyl]amino]3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 41.0 g of N,N-dimethyl-p-phenylenediamine, 100 ml of N,N-dimethylaniline, and 23.6 g of 2,6-dichloro-3-nitrobenzoic acid was heated for seven hours on a steam bath. The resulting cake was suspended in dichloromethane, filtered, and the solid washed with water. Recrystallization from DMF-ethanol provided 6-chloro-2[[4-(dimethylamino)phenyl]amino]3-nitrobenzoic acid, mp 222°-223° C. (dec).

Workup

  1. temperaturewas heated for seven hours on a steam bath
  2. filtrationfiltered
  3. washthe solid washed with water
  4. customRecrystallization from DMF-ethanol

Sources & evidence

ORD record
ord-81b2d8c7a97747c09de52c96f2a74a3d
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Linked notes

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