N,N-Dimethylaniline → 3-Nitrobenzoic acid

HRID 1248836Notes

Reaction equation

HRID 1248836 reaction equation
CCOC1C=CC(N)=CC=1.Cl[C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17](Cl)[C:13]=1[C:14]([OH:16])=[O:15].CN(C)C1C=CC=CC=1>C(Cl)(Cl)Cl>[N+:21]([C:20]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 90764-EthoxyanilineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 84973-Nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 28.0 g (0.20 mol) of p-phenetidine, 23.6 g (0.10 mol) of 2,6-dichloro-3-nitrobenzoic acid, and 80 ml of N,N-dimethylaniline was heated five hours on a steam bath. The resulting mixture was diluted with chloroform and extracted with 1N aq. NaOH. Acidification of the aqueous extract yielded 6-chloro-2-[4-ethoxyphenyl)amino]-3-nitrobenzoic acid as reddish brown crystals, mp 174°-176° C.

Workup

  1. temperaturewas heated five hours on a steam bath
  2. extractionextracted with 1N aq. NaOH
  3. extractionAcidification of the aqueous extract

Sources & evidence

ORD record
ord-8522202304b74cb0980ca15eed7674b6
Source dataset
uspto-grants-1986_12
Patent number
US04626540

Reaction notes

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