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

HRID 2261949Notes

Reaction equation

HRID 2261949 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 100%

Procedure

A solution of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (75 g, 0.25 mol) in ammonium hydroxide 28% (250 mL) was heated to 85° C. for four days. Additions of ammonium hydroxide 28% (80 ml) were made three times daily. The solution was partially concentrated in-vacuo, then cooled in an ice bath. To the solution was added 6N hydrochloric acid until the pH became weakly acidic. The solid which formed was collected by vacuum filtration, washed twice with water (250 mL) and dried to afford 2-(4-amino-3-nitrobenzoyl)benzoic acid (72 g, 100%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.09 (br s, 3H), 7.99 (d, 1H), 7.75-7.58 (m, 3H), 7.40 (d, 1H), 7.09 (d, 1H); MS (EI) for C14H10N2O4: 309 (MNa+)

Workup

  1. temperaturecooled in an ice bath
  2. customThe solid which formed
  3. filtrationwas collected by vacuum filtration
  4. washwashed twice with water (250 mL)
  5. customdried

Sources & evidence

ORD record
ord-f54018ec4b9e460ba9ea8ab0395244f1
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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