Sodium Bicarbonate → HCID 15293228, compound

HRID 233025Notes

Reaction equation

HRID 233025 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[CH2:11][CH2:10][C:9]2=[O:21])=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+]>Br>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH2:11][CH2:10][C:9]2=[O:21])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23361269HCID 23361269, compound

Product 1

HCID 15293228HCID 15293228, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

To a suspension of petroleum ether washed sodium hydride (80% oil dispersion, 0.94 g) in dry dimethylformamide (30 ml) was added 5-(3-methoxyphenyl)-2-pyrrolidinone (2.5 g) followed by 4-picolyl chloride hydrochloride (2.3 g) at ambient temperature, under nitrogen. The solution was warmed at 60° C. for 0.5 hr and allowed to cool to ambient temperature. The reaction mixture was quenched with ammonium chloride solution, water, and ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate (5 times). The combined organic extracts were concentrated, the residue was diluted with a small volume of ethyl acetate, and the solution was washed with water (2 times). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give 2.9 g (78%) of 1-(4-pyridinylmethyl)-5-(3-methoxyphenyl)-2-pyrrolidinone. 1-(4-pyridinylmethyl)-5-(3-methoxyphenyl)-2-pyrrolidinone (2.9 g) in 48% hydrobromic acid (40 ml) was heated at 100° C. for 5.5 hrs. The reaction mixture was cooled to ambient temperature, neutralized with saturated sodium bicarbonate solution, and extracted with dichloromethane (3 times). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtration was concentrated. The residue was purified by flash column chromatography (silica gel, ether/0-20% methanol). The appropriate fractions were collected and concentrated to give 2.3 g (81%) of 1-(4-pyridinylmethyl)-5-(3-hydroxyphenyl)-2-pyrrolidinone.

Workup

  1. extractionextracted with dichloromethane (3 times)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. filtrationthe filtration
  5. concentrationwas concentrated
  6. customThe residue was purified by flash column chromatography (silica gel, ether/0-20% methanol)
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6472d2587f514707af245284daf3ca3f
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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