Hydrochloric Acid → 3-(2'-Methoxybenzylidene)-2-pyrrolidone

HRID 2085232Notes

Reaction equation

HRID 2085232 reaction equation
[H-].[Na+].C([N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])(=O)C.[CH:12](=O)[C:13]1[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl>O1CCCC1.O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]=[C:8]1[CH2:9][CH2:10][NH:6][C:7]1=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 86582-MethoxybenzaldehydeHCID 24758Sodium hydrideHCID 702662-Pyrrolidinone, 1-acetyl-

Product 1

HCID 2641593-(2'-Methoxybenzylidene)-2-pyrrolidoneYield 11.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (16 g) was suspended in tetrahydrofuran (100 ml) and a solution of N-acetylpyrrolidone (25 g) and o -anisaldehyde (26.8 g) in tetrahydrofuran (100 ml) was added dropwise under ice-cooling. After completion of the reaction, the reaction mixture was poured into water. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to give oily 3-(2′-methoxybenzylidene)-2-pyrrolidone (4.7 g). The oil was dissolved in methylene chloride (60 ml). By demethylation using boron tribromide under ice-cooling, 3-(2′-hydroxybenzylidene)-2-pyrrolidone (4.0 g) was obtained as yellow crystals. To the crystals (1.5 g) were added dimethylformamide (50 ml) and potassium carbonate (2.2 g). (S)-Glycidyl nosylate (2.3 g) was added and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure and water was added. The mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate to give an oily compound (1.8 g). By the reaction of the oil (0.5 g) and 4-(5,6,7,8-tetrahydronaphthalen-2-yl)piperidine (0.5 g) in methanol in the same manner as in Example 307, the title compound (0.4 g) was obtained, melting point 157-159° C.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a6828aafdd18410bb77f75a295846793
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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