Water → HCID 15135645, compound

HRID 359487Notes

Reaction equation

HRID 359487 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.Cl[C:10]1[C:15]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:14][CH:13]=[CH:12][N:11]=1.O>C1(C)C=CC=CC=1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:15]2[C:10]([N:5]3[CH2:6][CH2:7][CH2:8][C:4]3=[O:3])=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 14796245HCID 14796245, compound

Product 1

HCID 15135645HCID 15135645, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1.3 g of 60% sodium hydride in 20 ml of toluene is added 5.1 g of 2-oxopyrrolidine, followed by addition of 7.4 g of 2-chloro-3-(4-methoxybenzoyl)pyridine. The mixture is stirred at 50° C. for 1 hour. After the reaction mixture is poured into water, the toluene layer is washed with water and the solvent thereof is distilled off. The residue is recrystallized from a mixed solvent of isopropyl ether and ethyl acetate to give 3-(4-methoxybenzoyl)-2-(2-oxopyrrolidin-1-yl)pyridine, m.p. 76°-77° C.

Workup

  1. washthe toluene layer is washed with water
  2. distillationthe solvent thereof is distilled off
  3. customThe residue is recrystallized from a mixed solvent of isopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-f01b89c5cdba4f6ebd70515855ee996a
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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