Water → 6-(3-Hydroxypropoxy)nicotinonitrile

HRID 734427ノート

反応式

HRID 734427 の反応式
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].Cl[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1.O>CN(C=O)C>[OH:6][CH2:5][CH2:4][CH2:3][O:7][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1

参加物

6

反応物 4

HCID 962WaterHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrile

生成物 1

HCID 431521396-(3-Hydroxypropoxy)nicotinonitrile収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (0.42 g, 60% suspension in mineral oil, 10.61 mmol) was added to a solution of 1,3-propanediol (2.30 mL, 31.83 mmol) in DMF (22 mL) at 0° C., and the mixture was stirred at rt for 20 minutes. To the resultant pale yellow slurry was added 6-chloronicotinonitrile (1.50 g, 10.61 mmol) in one portion. The mixture was stirred at rt for 18 h. It was then poured into water. The precipitates were filtered and the filtrate was extracted with ethyl acetate. The organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (1.56 g, 83%) as a white solid. 1H NMR (300 MHz, CD2Cl2) δ 8.47 (d, 1H), 7.82-7.79 (m, 1H), 6.84-6.82 (m, 1H), 4.53 (t, 2H), 3.75 (t, 2H), 2.06-1.99 (m, 2H).

後処理

  1. stirringThe mixture was stirred at rt for 18 h
  2. filtrationThe precipitates were filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7fc2969898564c098ca82b381c016147
出典データセット
uspto-grants-2009_09
特許番号
US07592361B2

反応ノート

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