Water → 1-Methyl-4-nitro-1H-indazole

HRID 586072

反応式

HRID 586072 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][NH:10]2)([O-:5])=[O:4].[CH3:15]I.O>CN(C=O)C>[CH3:15][N:10]1[C:11]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[N:9]1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 180574-NitroindazoleHCID 24758Sodium hydride

生成物 1

HCID 2802131-Methyl-4-nitro-1H-indazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A suspension of NaH (1.1 g, 32.2 mmol; 60% dispersion in mineral oil) in DMF (40 mL) was treated with 4-nitro-1H-indazole (5 g, 30.6 mmol) in DMF (40 mL) at 0° C. After stirring for 30 minutes, the mixture was treated with methyl iodide (4.6 g, 32.18 mmol) in DMF (20 ml) drop wise. The mixture was allowed to gradually warm to ambient temperature and stir overnight. The mixture was poured into water (250 ml) and extracted with ethyl acetate (2×100 mL). The organics were combined, washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was chromatographed (SiO2, ethyl acetate/hexanes) to provide the title compound. 1H NMR (DMSO-d6) δ 8.50 (s, 1H), 8.24 (d, 1H), 8.19 (d, 1H), 7.65 (t, 1H).

後処理

  1. stirringstir overnight
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was chromatographed (SiO2, ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-20db3f0d822d4d408ae7611a7ad968f2
出典データセット
uspto-grants-2005_08
特許番号
US06933311B2

関連ノート

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