Sodium Bicarbonate → HCID 15293228, compound

HRID 742572Notes

Reaction equation

HRID 742572 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:12](=[O:21])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:12](=[O:21])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=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

A solution of 5-(3-methoxyphenyl)-1-(4-pyridinylmethyl)-2-pyrrolidinone (2.9 g) and 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 filtrate 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 product. Recrystallization from ether/methanol gave the analytical sample, mp 148°-150° C.

Workup

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

Sources & evidence

ORD record
ord-1d259f2ce9414aed98aebabf14f943c3
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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