Pyrrolidine → HCID 18987731, compound

HRID 1463274Notes

Reaction equation

HRID 1463274 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])(=[O:3])[CH3:2].[CH3:13][C:14]([CH:16]([O:19][CH3:20])[O:17][CH3:18])=O.N1CCCC1>C1(C)C=CC=CC=1>[CH3:18][O:17][CH:16]([O:19][CH3:20])[C:14]1([CH3:13])[CH2:2][C:1](=[O:3])[C:4]2[CH:5]=[C:6]([C:7]#[N:8])[CH:9]=[CH:10][C:11]=2[O:12]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 80650Pyruvic aldehyde dimethyl acetalHCID 123328323-Acetyl-4-hydroxybenzonitrile

Product 1

HCID 18987731HCID 18987731, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 100 ml of toluene were dissolved 8.06 g (50 mmole) of 3-acetyl-4-hydroxybenzonitrile and 7.68 g (65 mmole) of pyruvic aldehyde dimethyl acetal; and, 1.67 ml (20 mmole) of pyrrolidine was added at room temperature thereto. 30 Minutes thereafter, the reactants were heated to reflux for 8 hours using Dean-Stark apparatus. The solvent was removed under reduced pressure; and, 50 ml of 2N HCl solution was added to the residue so obtained. The resultant solution was stirred for 30 minutes at room temperature, extracted with ethyl acetate (100 ml×2), washed with 50 ml of water and then with 50 ml of saturated sodium chloride aqueous solution and purified by silica gel column chromatography using as an eluent a mixture of hexane and ethyl acetate (4:1) to obtain 11.19 g (yield 86%) of the title compound as a white solid.

Workup

  1. temperature30 Minutes thereafter, the reactants were heated
  2. temperatureto reflux for 8 hours
  3. customThe solvent was removed under reduced pressure
  4. additionand, 50 ml of 2N HCl solution was added to the residue
  5. customso obtained
  6. extractionextracted with ethyl acetate (100 ml×2)
  7. washwashed with 50 ml of water
  8. customwith 50 ml of saturated sodium chloride aqueous solution and purified by silica gel column chromatography
  9. additiona mixture of hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-8a97b85bb2924f1682a6104e7e42387f
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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