Hydrochloric Acid → 4-Anilino-3-nitrobenzoic acid

HRID 28663

Reaction equation

HRID 28663 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C(O)C.O>[NH:14]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 38243664-Anilino-3-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Fluoro-3-nitrobenzoic acid (21.6 mmol) and an aniline (43.2 mmol) in 15 mL of ethanol were stirred at reflux under argon for 5 h resulting in the formation of an orange precipitate. After 12 h the heterogeneous reaction mixture was poured into 50 mL of 1N HCl(aq) and diluted with 100 mL of water. The solution was stirred for 20 min then the precipitate filtered to yield the 4-anilino-3-nitrobenzoic Acid: e.g. 4-{[3-(benzyloxy)phenyl]amino}-3-nitrobenzoic acid.

Workup

  1. temperatureat reflux under argon for 5 h
  2. customresulting in the formation of an orange precipitate
  3. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-8ab56e89eb204695b2ea7c0c30ec3f5d
Source dataset
uspto-grants-2008_09
Patent number
US07419995B2

Linked notes

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