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

HRID 335488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335488
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 4069086(R,S)-1-METHYL-3-NICOTINOYLPYRROLIDONEAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d13ed127897f48ddba8b122ab73a84a6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884021B2

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