Hydrochloric Acid → 3-(5-Bromo-pyridin-2-yl)-1-methyl-pyrrolidin-2-one

HRID 1425995Notes

Reaction equation

HRID 1425995 reaction equation
[OH-].[Na+].C(OC([C:8]1([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=2)[CH2:12][CH2:11][N:10]([CH3:13])[C:9]1=[O:14])=O)C.Cl>C(O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]2[CH2:12][CH2:11][N:10]([CH3:13])[C:9]2=[O:14])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 679978383-(5-Bromo-pyridin-2-yl)-1-methyl-2-oxo-pyrrolidine-3-carboxylic acid ethyl ester

Product 1

HCID 679978423-(5-Bromo-pyridin-2-yl)-1-methyl-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous NaOH solution (1 mol/L, 3 mL) was added to 3-(5-bromo-pyridin-2-yl)-1-methyl-2-oxo-pyrrolidine-3-carboxylic acid ethyl ester (0.50 g) in ethanol (10 mL) at room temperature. The solution was stirred at room temperature overnight and then neutralized with 1 M aqueous hydrochloric acid. The resulting mixture was concentrated and the residue was taken up in ethyl acetate and filtered to remove the non-dissolving parts. The filtrate was dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (ethyl acetate/methanol 9:1) to give the title compound as a colorless oil. Yield: 0.28 g (71% of theory); Mass spectrum (ESI+): m/z=255/257 (Br) [M+H]+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. filtrationfiltered
  3. customto remove the non-dissolving parts
  4. dry with materialThe filtrate was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-f4119be3b4c34d98b5b85ab69663b377
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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