Ammonia → 2-Carbamoyl-3-nitrobenzoic acid

HRID 1870931

反応式

HRID 1870931 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
300 °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 300° 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 vacuo 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 vacuo

出典と根拠

ORDレコード
ord-8f68f01615034c159b981bb4c747971f
出典データセット
uspto-grants-2000_08
特許番号
US06100283

関連ノート

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