P-Anisidine → 6-Chloro-2-(4-methoxyanilino)-3-nitrobenzoic acid

HRID 1248834Notes

Reaction equation

HRID 1248834 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl[C:11]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:12]=1[C:13]([OH:15])=[O:14]>>[Cl:23][C:16]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 27780126-Chloro-2-(4-methoxyanilino)-3-nitrobenzoic acidYield 79.5%

Conditions

Temperature
75 °C

Procedure

To 74 g (0.60 mol) of p-anisidine stirred mechanically at 75° C. was added 35.4 g (0.15 mol) of 2,6-dichloro-3-nitrobenzoic acid [Lehmstedt and Schrader, Berichte 70B, 1526 (1937)] in small portions over one-half hour. The mixture was heated at 75° C. for 24 hours with stirring during the first two hours. The reaction mixture was cooled and the resulting solid mass was triturated in a mechanical blender with 300 ml of 2.4N hydrochloric acid. The solid was collected, washed with 3N hydrochloric acid, stirred in 400 ml of 0.5N sodium carbonate, and filtered. The filtrate, diluted with 250 ml of water, was gradually acidified with 4N hydrochloric acid. The precipitate was collected, washed with water, and dried to provide 38.5 g (79%) of the red title compound, mp 205°-213° C. A purified sample, from toluene, melts at 212°-215° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting solid mass was triturated in a mechanical blender with 300 ml of 2.4N hydrochloric acid
  3. customThe solid was collected
  4. washwashed with 3N hydrochloric acid
  5. stirringstirred in 400 ml of 0.5N sodium carbonate
  6. filtrationfiltered
  7. additionThe filtrate, diluted with 250 ml of water
  8. customThe precipitate was collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-4657a9722ffa4a5b9009217a046077b8
Source dataset
uspto-grants-1986_12
Patent number
US04626540

Reaction notes

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