Water → N-methyl-2-pyrrolidone

HRID 1699960Notes

Reaction equation

HRID 1699960 reaction equation
O.[CH2:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.[CH3:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10]>>[OH:6][CH2:7][CH2:2][CH2:3][C:4]([OH:5])=[O:10].[CH3:12][N:11]1[C:9](=[O:10])[CH2:8][CH2:2][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 7302Gamma-ButyrolactoneHCID 31374Dimethylacetamide

Product 2

HCID 104134-Hydroxybutyric AcidHCID 13387N-methyl-2-pyrrolidoneYield 60%

Procedure

JP-A-1 186 864 (Derwent Abstr. 89-259000/36) discloses the preparation of N-alkylated lactams by reaction of the corresponding lactones with secondary amines in the presence of water via the corresponding N,N-dialkyl-omega-hydroxycarboxamides as intermediates. According to Example 1 of this patent application, the reaction of γ-BL with aqueous DMA gives an NMP yield of 60% and additionally forms methylamides of γ-hydroxybutyric acid. In the single further example according to the application, too, an NMP yield of 60% is reported for the corresponding reaction of γ-BL with DMA.

Sources & evidence

ORD record
ord-528f1c1c2fb14619b03d9b1a7625817e
Source dataset
uspto-grants-2002_02
Patent number
US06348601B2

Reaction notes

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