Hydrochloric Acid → 2-(4-Amino-3-nitrobenzoyl)benzoic acid

HRID 2367084Notes

Reaction equation

HRID 2367084 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].Cl.[OH-].[NH4+:24]>>[NH2:24][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium Hydroxide2×HCID 665622-(4-Chloro-3-nitrobenzoyl)benzoic acid

Product 1

HCID 27975222-(4-Amino-3-nitrobenzoyl)benzoic acidYield 95%

Procedure

A solution of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (38.5 g, 0.126 mol) in ammonium hydroxide (33% wt, 200 mL) was heated to a gentle reflux and stirred for 24 h. An additional ammonium hydroxide (200 mL) was added every 5 h within the 24 h reaction time period. The reaction mixture was cooled to room temperature and was added 6N aqueous hydrochloric acid until pH reached 2. The precipitated yellow solid was collected by filtration and washed with water then dried in vacuo to provide 2-[(4-amino-3-nitrophenyl)carbonyl]benzoic acid (38.8 g, 95%). 1H NMR (400 MHz, CD3OD): 8.27 (d, 1H), 8.11 (d, 1H), 7.80 (dd, 1H), 7.72 (td, 1H), 7.65 (td, 1H), 7.39 (d, 1H), 7.01 (d, 1H); MS (EI) for C14H10N2O5: 309 (MNa+).

Workup

  1. temperaturea gentle reflux
  2. filtrationThe precipitated yellow solid was collected by filtration
  3. washwashed with water
  4. customthen dried in vacuo

Sources & evidence

ORD record
ord-c96e885f908e4549a623fb822ee68915
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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