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

HRID 537139

反応式

HRID 537139 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 115718843-amino-1H-indazole-5-carboxylic Acid収率 58.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e0b6aea40fa14edd8313bb2ccaa04762
出典データセット
uspto-grants-2014_10
特許番号
US08859773B2

関連ノート

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