Nicotinic Acid → N-Methoxy-N-methylnicotinamide

HRID 593507

反応式

HRID 593507 の反応式
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:14][O:15][NH:16][CH3:17].C(N(CC)CC)C>>[CH3:17][N:16]([O:15][CH3:14])[C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

参加物

5

反応物 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 24386Thionyl Chloride

生成物 1

HCID 10558996N-Methoxy-N-methylnicotinamide

実験手順

A flask is charged with nicotinic acid (5.0 g, 40.6 mmol). Thionyl chloride (30.0 mL) is added and the reaction is refluxed for 1 h. It is then cooled to room temperature and concentrated in vacuo. The residue is dissolved in anhydrous dichloromethane (30 mL) and O,N-dimethyl-hydroxylamine (4.35 g, 44.0 mmol) is added, followed by addition of triethylamine (14.15 g, 100.0 mmol). The reaction mixture is stirred at room temperature for 1.5 h. It is then washed with water and the aqueous phase is extracted with dichloromethane. The combined organic layer is dried over sodium sulfate and concentrated in vacuo to afford N-methyl-N-methoxy-nicotinamide as a brown oil. MS (ESI) m/z 167.0 (M+H)+.

後処理

  1. temperaturethe reaction is refluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in anhydrous dichloromethane (30 mL)
  4. washIt is then washed with water
  5. extractionthe aqueous phase is extracted with dichloromethane
  6. dry with materialThe combined organic layer is dried over sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cdf6e6329b7044669a3248a1d08e0744
出典データセット
uspto-grants-2016_01
特許番号
US09242963B2

関連ノート

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