Water → 6-(3-Hydroxypropoxy)nicotinonitrile

HRID 603448ノート

反応式

HRID 603448 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, 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 min. To the resultant heterogeneous mixture was added 6-chloronicotinonitrile (1.50 g, 10.6 mmol) in one portion. The mixture was stirred at rt for 18 h, poured into water, and filtered. The filtrate was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give the product (1.56 g, 83%) as a white solid. 1H NMR (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. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f7633a5486764f33b239a73efeb877a7
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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