Sodium hydride → 5-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-one

HRID 598161ノート

反応式

HRID 598161 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][NH:14]2.Br[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25].[H-].[Na+]>CN1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][N:14]2[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 672672585-(2,4-Dimethylphenyl)-3-methylcinnolin-4(1H)-one

生成物 1

HCID 589385695-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-one収率 75%

試薬・触媒・溶媒 1

HCID 84541-Methylpyrrolidine溶媒

実験手順

To 0.041 g (0.16 mmol) of 5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one in 0.5 mL of N-methylpyrrolidine was added 0.069 mL of 4-bromoheptane and 0.012 g (0.31 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 75 min. at room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with a 8% ethyl acetate/hexanes mixture to give 0.042 g (75%) of the title compound as a light green-yellow semisolid.

後処理

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organics were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with a 8% ethyl acetate/hexanes mixture

出典と根拠

ORDレコード
ord-4c6d66c81a604cbdb3c98764ce69fe95
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

反応ノート

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