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

HRID 335488Notes

Reaction equation

HRID 335488 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d13ed127897f48ddba8b122ab73a84a6
Source dataset
uspto-grants-2014_11
Patent number
US08884021B2

Reaction notes

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