Ethanol → 1-benzyl-3-cyclopropyl-1H-indazol-4-amine

HRID 79264ノート

反応式

HRID 79264 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH:20]2[CH2:22][CH2:21]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([CH:20]2[CH2:21][CH2:22]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 672600391-benzyl-3-cyclopropyl-4-nitro-1H-indazole

生成物 1

HCID 672597331-benzyl-3-cyclopropyl-1H-indazol-4-amine収率 66.7%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

To a reaction flask was added 1-benzyl-3-cyclopropyl-4-nitro-1H-indazole (60.0 mg, 0.205 mmol), iron powder (114 mg, 2.05 mmol) and ammonium chloride (10.9 mg, 0.205 mmol). Ethanol (0.8 mL) and water (0.2 mL) were added and the mixture was heated at 85° C. with stirring for 60 minutes. The solvent was removed under reduced pressure. Ethyl acetate (0.8 mL) and triethylamine (0.2 mL) was added and the mixture was heated at 60° C. for 10 minutes. The mixture was filtered through glass fiber filter paper, washing with methanol and ethyl acetate. The filtrate was concentrated under reduced pressure. The material was purified by preparative chromatography, eluting with 3% methanol in dichloromethane, containing 0.5% ammonium hydroxide solution to give 1-benzyl-3-cyclopropyl-1H-indazol-4-amine (36 mg).

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionEthyl acetate (0.8 mL) and triethylamine (0.2 mL) was added
  3. temperaturethe mixture was heated at 60° C. for 10 minutes
  4. filtrationThe mixture was filtered through glass fiber
  5. filtrationfilter paper
  6. washwashing with methanol and ethyl acetate
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe material was purified by preparative chromatography
  9. washeluting with 3% methanol in dichloromethane
  10. additioncontaining 0.5% ammonium hydroxide solution

出典と根拠

ORDレコード
ord-059cd12138994b049a25a5e13fbb0f92
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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