N,N-Dimethylaniline → 4H-pyran-4-one

HRID 649304Notes

Reaction equation

HRID 649304 reaction equation
C[C:2]1([CH3:10])[O:7][C:6](=O)[CH:5]=[C:4](C)[O:3]1.[CH:11]([NH:13][C:14](=[O:19])[CH2:15][C:16]([CH3:18])=O)=O.CN(C)C1C=CC=CC=1>>[NH:13]1[CH:11]=[CH:18][CH:16]=[CH:15][C:14]1=[O:19].[O:7]1[CH:6]=[CH:5][C:4](=[O:3])[CH:10]=[CH:2]1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one2×HCID 365127HCID 365127, compound

Product 2

HCID 79684H-pyran-4-oneHCID 88712-Pyridone

Procedure

In addition, the reaction for obtaining an 4-pyrone compound from 2,2,6-trimethyl-1,3-dioxin-4-one has been known. That is, T. Kato et al [Chem, Pharm. Bull., 30, 1315(1982)] studied on the reaction between amides or acetoacetyl derivatives thereof and 2,2,6-trimethyl-1,3-dioxin-4-one and reported that the reaction of N-formylacetoacetamide with 2,2,6-trimethyl-1,3-dioxin-4-one in the presence of N,N-dimethylaniline gave a pyridone compound as the main product and 4-pyrone compound as the by-product.

Sources & evidence

ORD record
ord-35d0be8732aa4ce7a354f5b9b963e699
Source dataset
uspto-grants-1988_04
Patent number
US04739083

Reaction notes

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