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

HRID 280259Notes

Reaction equation

HRID 280259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].Cl[C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([Cl:24])[C:13]=1[C:14]([OH:16])=[O:15].CN(C)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:24][C:17]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:2]([Cl:1])[CH:3]=2)[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 214413-Chloro-4-methoxyanilineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 135883476-Chloro-2-[(3-chloro-4-methoxyphenyl)amino]-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 30 g of 3-chloro-4-methoxyaniline, 18.9 g of 2,6-dichloro-3-nitrobenzoic acid, and 150 ml N,N-dimethylaniline was heated at 100° under nitrogen for 24 hours. The reaction mixture was dissolved in chloroform and washed with dilute ammonium hydroxide. After the aqueous layer was washed with chloroform, it was acidified and the resulting orange solid was collected to provide 6-chloro-2[(3-chloro-4-methoxyphenyl)amino]-3-nitrobenzoic acid, mp 222°-228° C.

Workup

  1. temperaturewas heated at 100° under nitrogen for 24 hours
  2. washwashed with dilute ammonium hydroxide
  3. washAfter the aqueous layer was washed with chloroform, it
  4. customthe resulting orange solid was collected

Sources & evidence

ORD record
ord-2b9a38beeb7c47feb5cac4c6de898dbd
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Reaction notes

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