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

HRID 252858

반응식

HRID 252858 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acid수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-530bcd613205464fa33ccf126ac3574c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868205B2

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