Hydrochloric Acid → (R,S)-1-METHYL-3-NICOTINOYLPYRROLIDONE

HRID 335488ノート

反応式

HRID 335488 の反応式
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:12][N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18].[H-].[Na+].Cl>C1(C)C=CC=CC=1.CO>[CH3:12][N:13]1[CH2:17][CH2:16][CH:15]([C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)[C:14]1=[O:18]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 69188Ethyl Nicotinate

生成物 1

HCID 4069086(R,S)-1-METHYL-3-NICOTINOYLPYRROLIDONE収率 83.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

Ethyl nicotinate (10.3 g, 66 mmol) and N-methyl-2-pyrrolidone (6.5 mL, 66 mmol) were dissolved in a dry toluene (200 mL) and sodium hydride (4 g) was added therein in batch. The mixture was stirred for 30 h under reflux, and then cooled to room temperature, and 5 mL methanol was added to quench the reaction. The reaction solution was poured into 1 mol/L of diluted hydrochloric acid (70 mL), extracted with dichloromethane. The extract was washed with saline and concentrated till dry to give 11.3 g colorless oily product (1-methyl-3-nicotinoyl-2-pyrrolidone) with a yield of 81%. 1HNMR (CD3OD, 300 MHz) δ: 9.21 (d, 1H), 8.75 (dd, 1H), 8.48 (dt, 1H), 7.60 (dd, 1H), 4.70 (d, 1H), 3.48-3.57 (m, 1H), 3.41-3.46 (m, 1H), 2.85 (s, 3H), 2.52-2.60 (m, 1H), 2.30-2.38 (m, 1H); ESI-MS 205.0 (M+H), 243.1 (M+K).

後処理

  1. additionwas added
  2. temperatureunder reflux
  3. customto quench
  4. customthe reaction
  5. extractionextracted with dichloromethane
  6. washThe extract was washed with saline
  7. concentrationconcentrated
  8. customtill dry

出典と根拠

ORDレコード
ord-d13ed127897f48ddba8b122ab73a84a6
出典データセット
uspto-grants-2014_11
特許番号
US08884021B2

反応ノート

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