Ammonia → 2-Carbamoyl-3-nitrobenzoic acid

HRID 382347

Reaction equation

HRID 382347 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=[O:8])([O-:3])=[O:2].N.C([O-])(=O)C1C(=CC=CC=1)C([NH2:21])=O.[NH4+]>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:10]([NH2:21])=[O:11])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 216313-Nitrophthalic anhydrideHCID 3083555Ammonium 2-(aminocarbonyl)benzoate

Product 1

HCID 4375472-Carbamoyl-3-nitrobenzoic acid

Conditions

Temperature
30 °C

Procedure

3-Nitrophthalic anhydride (10.0 g, 50 mmol) was added in portions over 20 minutes to concentrated aqueous ammonia solution (15 ml), and the mixture was stirred at 30° C. for a further 30 minutes. The crystalline mass of ammonium phthalamate, deposited upon cooling the pale yellow solution, was collected and redissolved in a minimum amount of warm water. Concentrated hydrochloric acid (4.5 ml) was added dropwise, with stirring, and the resulting paste was washed with water, and dried in vacua to give 3-nitrophthalamic acid as a fine white powder. (9.01 g, 83%), m.p. 217° C. Found: C, 45.76; H, 2.79; N, 13.21. C8H6N2O5 requires C, 45.71; H, 2.86; N, 13.33%; vmax/cm−1 3466.52, 3321.84, 1668.64, 1604.98, and 1525.89; δH (d6-DMSO, 200 MHz) 7.75 (1H, br s, CONH), 7.8 (1H, t, Ar-5H), 8.16 (1H, brs, CONH), 8.2 (1H, d, Ar-6H), 8.3 (1H, d, Ar-4H); δC (d6-DMSO) 127.32, 130.06, 132.28, 133.49, 134.78, 147.71, 166.25, and 166.60; m/z (EI) 192 (M+−1), 177, 149, 103, 75.

Workup

  1. temperatureupon cooling the pale yellow solution
  2. customwas collected
  3. dissolutionredissolved in a minimum amount of warm water
  4. additionConcentrated hydrochloric acid (4.5 ml) was added dropwise
  5. stirringwith stirring
  6. washthe resulting paste was washed with water
  7. customdried in vacua

Sources & evidence

ORD record
ord-a9b598bfa42e4ccda7cc03d0593a5c0e
Source dataset
uspto-grants-2001_10
Patent number
US06310082B1

Linked notes

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