Ammonia → 2-Carbamoyl-3-nitrobenzoic acid

HRID 382347

反応式

HRID 382347 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

HCID 4375472-Carbamoyl-3-nitrobenzoic acid

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a9b598bfa42e4ccda7cc03d0593a5c0e
出典データセット
uspto-grants-2001_10
特許番号
US06310082B1

関連ノート

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