Water → 4-(Methylamino)-3-nitrobenzoic acid

HRID 252858

反応式

HRID 252858 の反応式
[CH3:1][NH2:2].O.F[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]>CN(C=O)C>[CH3:1][NH:2][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]

参加物

5

反応物 3

HCID 962WaterHCID 6329MethylamineHCID 679874-Fluoro-3-nitrobenzoic acid

生成物 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acid収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 40% solution of methylamine in water (11 mL; 128 mmol) (or any other primary amine) was slowly added to a stirring suspension of 4-fluoro-3-nitrobenzoic acid (278, 6.1 g; 32.9 mmol) in DMF (20 mL) at room temperature. After the addition was completed the mixture was stirred at the same temperature for 60 min; concentrated in vacuo, and suspended in 5% KHSO4 (final pH=2). The suspension was stirred overnight; the precipitate was collected by filtration, washed with water, then with ether and dried to afford the title compound 279 (6.5 g; 100% yield). 1H NMR: (400.2 MHz, DMSO) δ (ppm): 12.8 (bs; 1H), 8.59 (d, J=2.0 Hz; 1H); 8.55 (q, J=5.0 Hz; 1H); 7.96 (dd, J=2.0, 9.1 Hz; 1H); 7.04 (d, J=9.1 Hz; 1H); 3.00 (d, J=5.0 Hz; 3H). MS: calc: 196.2; found: 197.1 (M+H)

後処理

  1. additionAfter the addition
  2. concentrationconcentrated in vacuo
  3. stirringThe suspension was stirred overnight
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialwith ether and dried

出典と根拠

ORDレコード
ord-530bcd613205464fa33ccf126ac3574c
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

関連ノート

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