Hydrochloric Acid → 4-Anilino-3-nitrobenzoic acid

HRID 74145

Reaction equation

HRID 74145 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.C(O)C.Cl>O>[N+:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]([OH:8])=[O:7])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6115AnilineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 38243664-Anilino-3-nitrobenzoic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An eggplant flask was charged with 4-fluoro-3-nitrobenzoic acid (2.51 g, 13.56 mmol), aniline (2.52 g, 27.12 mmol), and ethanol (9.5 mL), and this was heated to reflux with stirring for 16 hours. After cooling to room temperature, the mixture was poured into dilute hydrochloric acid (1 M, 50 mL), diluted with distilled water (100 mL), was left to stir as is at room temperature for 30 minutes. The precipitated crystals were filtered off, and washed successively with dilute hydrochloric acid (1 M, with approx. 3 mL 3 times), distilled water (approx. 5 mL 2 times), and with diethyl ether (approx. 3 mL). The crystals obtained were dried at reduced pressure with heating to yield the title compound (3.39 g, quant.) as a reddish-orange solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. waitwas left
  4. stirringto stir
  5. waitas is at room temperature for 30 minutes
  6. filtrationThe precipitated crystals were filtered off
  7. washwashed successively with dilute hydrochloric acid (1 M, with approx. 3 mL 3 times)
  8. distillationdistilled water (approx. 5 mL 2 times)
  9. customThe crystals obtained
  10. customwere dried at reduced pressure
  11. temperaturewith heating

Sources & evidence

ORD record
ord-1e742260cb784dd8b2f181dcc70b9af3
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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