Hydrazine hydrate (1:1) → 2-(2-Amino-5-fluorophenyl)acetohydrazide

HRID 50000

반응식

HRID 50000 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O.[NH2:14][NH2:15]>>[NH2:7][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[CH2:5][C:6]([NH:14][NH2:15])=[O:11]

참가 물질

3

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 2365665-Fluoroisatin2회

생성물 1

HCID 690577422-(2-Amino-5-fluorophenyl)acetohydrazide

반응 조건

온도
110 °C

실험 절차

Hydrazine hydrate (55%, 3000 mL) and 5-fluoroisatin (300 g) were heated to 100° C. An additional 5-fluoro-isatin (500 g) was added in portions (100 g) over 120 minutes with stirring. The mixture was heated to 110° C. and stirred for 4 hours. The mixture was cooled to room temperature and the solids collected by vacuum filtration to give crude (2-amino-5-fluoro-phenyl)-acetic acid hydrazide (748 g). The hydrazide was suspended in water (700 mL) and the pH of the mixture adjusted to <pH 3 with 12 N hydrochloric acid. The mixture was stirred for 12 hours at room temperature. The solids were collected by vacuum filtration and washed twice with water. The product was dried under vacuum to give 5-fluoro-1,3-dihydro-indol-2-one (600 g, 73% yield) as a brown powder. 1H-NMR (dimethylsulfoxide-d6) δ3.46 (s, 2H, CH2), 6.75, 6.95, 7.05 (3×m, 3H, aromatic), 10.35 (s, 1H, NH). MS m/z 152 [M+1].

후처리

  1. stirringstirred for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe solids collected by vacuum filtration

출처 및 근거

ORD 기록
ord-b0ffcea2be874f39976f0c9c68ec97ac
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710067B2

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