Pyridine → 6-Isobutyl-5-methylnicotinonitrile

HRID 2065894ノート

反応式

HRID 2065894 の反応式
[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]([NH2:11])=O)=[CH:7][N:6]=1)[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]#[N:11])=[CH:7][N:6]=1)[CH:2]([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 1049PyridineHCID 670268976-Isobutyl-5-methylnicotinamide

生成物 1

HCID 670269756-Isobutyl-5-methylnicotinonitrile収率 78.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 6-isobutyl-5-methyl-nicotinamide (1.89 g, 9.85 mmol) in DCM (40 mL) and pyridine (2.83 g, 39.4 mmol), TFA anhydride (5.17 g, 24.6 mmol) is added portionwise at 0° C. The mixture is stirred at rt for 24 h, diluted with DCM and washed with water, 4% aq. citric acid solution followed by sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 6-isobutyl-5-methyl-nicotinonitrile (1.35 g) as a white solid; LC-MS: tR=0.89 min, [M+1]+=175.11.

後処理

  1. washwashed with water, 4% aq. citric acid solution
  2. extractionextract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

出典と根拠

ORDレコード
ord-ed548ffc34534ec9930bf45ed8a362cf
出典データセット
uspto-grants-2012_10
特許番号
US08288554B2

反応ノート

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