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

HRID 2367105Notes

Reaction equation

HRID 2367105 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-7d3724871c61468599e956b770bf36b1
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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