Hydrazine hydrate (1:1) → 4-Fluoro-2-methyl-1H-indol-5-amine

HRID 2222428ノート

反応式

HRID 2222428 の反応式
[F:1][C:2]1[C:10]([N:11]2C(=O)C3=CC=CC=C3C2=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:22])[NH:6]2.O.NN.C(NN)(=O)C1C(=CC=CC=1)C(NN)=O>CO>[NH2:11][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([CH3:22])=[CH:4]2

参加物

5

反応物 3

HCID 24654Hydrazine hydrate (1:1)HCID 11367556PhthalohydrazideHCID 597122384-Fluoro-2-methyl-5-phthalimidoindole

生成物 1

HCID 445584264-Fluoro-2-methyl-1H-indol-5-amine収率 76.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Fluoro-2-methyl-5-phthalimidoindole (1.2, 4 mmol) was dissolved in methanol (30 ml). Hydrazine monohydrate (260 μl, 5.3 mmol) was added and the reaction mixture was stirred at ambient temperature for 2 hours. The solvent was evaporated off and the residue taken up in methylene chloride. The phthalhydrazide by-product was removed by filtration and the filtrate purified by flash chromatography 0.5% methanol in methylene chloride. Evaporation of the solvent gave a white solid which contained traces of phthalhydrazide. Further purification was done by dissolving it in ethyl acetate, washing the organic phase with NaOH 2N and brine, drying over MgSO4. Rotary evaporation of the solvent gave 5-amino-4-fluoro-2-methylindole (500 mg, 76%).

後処理

  1. customThe solvent was evaporated off
  2. customThe phthalhydrazide by-product was removed by filtration
  3. customthe filtrate purified by flash chromatography 0.5% methanol in methylene chloride
  4. customEvaporation of the solvent
  5. customgave a white solid which
  6. customFurther purification
  7. dissolutionby dissolving it in ethyl acetate
  8. washwashing the organic phase with NaOH 2N and brine
  9. dry with materialdrying over MgSO4
  10. customRotary evaporation of the solvent

出典と根拠

ORDレコード
ord-009fa7e715004d1cb4ad344c5eb8e5d9
出典データセット
uspto-grants-2008_05
特許番号
US07371765B2

反応ノート

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