Pyrrolidine → HCID 19742841, compound

HRID 2254634Notes

Reaction equation

HRID 2254634 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])[CH:2]2[O:3][CH:1]2[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 19742841HCID 19742841, 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, then 1.67 ml (20 mmole) of pyrrolidine was added thereto at room temperature. 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 thereto. 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 with 50 ml of saturated sodium chloride aqueous solution, and purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (4:1) as an eluent to obtain 11.19 g (yield 86%) of the title compound in the form of a white solid.

Workup

  1. customat room temperature
  2. temperature30 minutes thereafter, the reactants were heated
  3. temperatureto reflux for 8 hours
  4. customthe solvent was removed under reduced pressure
  5. additionand, 50 ml of 2N HCl solution was added
  6. extractionextracted with ethyl acetate (100 ml×2)
  7. washwashed with 50 ml of water and with 50 ml of saturated sodium chloride aqueous solution
  8. custompurified by silica gel column chromatography
  9. additiona mixture of hexane and ethyl acetate (4:1) as an eluent

Sources & evidence

ORD record
ord-aefbc21ec8164313a041e555d8083ee8
Source dataset
uspto-grants-1993_08
Patent number
US05236935

Reaction notes

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