Water → Methyl 4[2-methyl-6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]benzoate

HRID 1276291Notes

Reaction equation

HRID 1276291 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:6].CC(C)([O-])C.[K+].O>CN(C=O)C>[CH3:14][C:12]1[C:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[CH:10][CH:9]=[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22115876HCID 22115876, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22115894Methyl 4[2-methyl-6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]benzoateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of methyl 4[6-(4-chlorobutanoylamino)-2-methylpyridin-3-yl]benzoate (D8, 0.60 g, 1.7 mmole) in DMF (7 ml) at 25° C. under argon was treated portionwise over 15 minutes with potassium t-butoxide (0.23 g, 2.0 mmole). The mixture was stirred for 3 h, then poured into water (100 ml) and extracted with ethyl acetate. The extract was washed with water, dried (Na2SO4) and concentrated in vacuo to afford the title compound as an orange solid (0.45 g, 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13c0d5e0568a4d0b817845cbcc5478be
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Reaction notes

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