Hydrazine hydrate (1:1) → 3-amino-1H-indazole-5-carboxylic Acid

HRID 537139

반응식

HRID 537139 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1F)[C:6]([OH:8])=[O:7])#[N:2].O.[NH2:14][NH2:15]>C(O)C>[NH2:2][C:1]1[C:3]2[C:11](=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[NH:15][N:14]=1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 27739323-Cyano-4-fluorobenzoic acid

생성물 1

HCID 115718843-amino-1H-indazole-5-carboxylic Acid수율 58.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 3-cyano-4-fluorobenzoic acid (980.0 mg, 5.94 mmol) in ethanol (6 mL), was added hydrazine hydrate (0.89 mL, 17.8 mmol). The reaction was heated at reflux for 3 hours. The reaction was cooled to room temperature and ethanol was removed under reduced pressure. The resultant yellow oil was taken up in water (50 mL) and basified with 1 N aqueous sodium hydroxide (5 mL). The solution was washed once with ethyl acetate (25 mL). The aqueous phase was acidified to pH=3 with 6 N aqueous hydrochloric acid and was allowed to stir at room temperature for 1 hour. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (612 mg, 48%) as a pink solid. +ESI (M+H) 178.1; 1H NMR (400 MHz, DMSO-d6, δ): 8.42-8.47 (m, 1H), 7.76 (dd, J=8.8, 1.6 Hz, 1H), 7.21 (d, J=8.8 Hz, 1H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 hours
  3. customethanol was removed under reduced pressure
  4. washThe solution was washed once with ethyl acetate (25 mL)
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-e0b6aea40fa14edd8313bb2ccaa04762
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859773B2

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