Methanol → HCID 577835, compound

HRID 1885621Notes

Reaction equation

HRID 1885621 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([N:7]2[C:11](=[O:12])[CH2:10][CH:9]([C:13]([OH:15])=[O:14])[CH2:8]2)=[CH:3][CH:2]=1.[CH3:17]O.S(=O)(=O)(O)O>C(Cl)Cl>[C:1]1([CH3:16])[CH:2]=[CH:3][C:4]([N:7]2[C:11](=[O:12])[CH2:10][CH:9]([C:13]([O:15][CH3:17])=[O:14])[CH2:8]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27418275-Oxo-1-p-tolyl-pyrrolidine-3-carboxylic acid

Product 1

HCID 577835HCID 577835, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Tolyl)-5-oxo-3-pyrrolidinecarboxylic acid (45.50 g) is suspended in methylene chloride (460 ml) and thereto are added methanol (50.5 ml) and conc. sulfuric acid (0.77 ml) and the mixture is refluxed for 19 hours. After cooling, the reaction mixture is concentrated under reduced pressure and the resulting residue is neutralized by adding water and aqueous sodium hydrogen carbonate solution thereto. The precipitated crystal is collected by filtration and washed with water to give the desired product (46.07 g), m.p. 71°-74° C.

Workup

  1. temperaturethe mixture is refluxed for 19 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. additionby adding water and aqueous sodium hydrogen carbonate solution
  5. filtrationThe precipitated crystal is collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-efb1440428bc4feb972b93cda69fe5a1
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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