2-Pyridone → HCID 9926549, compound

HRID 1885214Notes

Reaction equation

HRID 1885214 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]([CH:12]=[O:13])=[C:10](Br)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]#[N:16])[CH:8]=2)[O:3]1.P(Br)(Br)Br.[NH:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]1=[O:28].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C=O)C>[CH3:1][C:2]1([CH3:17])[C:11]([CH:12]=[O:13])=[C:10]([N:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]2=[O:28])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]#[N:16])[CH:8]=2)[O:3]1

Participants

8

Reactant 4

HCID 88712-PyridoneHCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 11779071HCID 11779071, compound

Product 1

HCID 9926549HCID 9926549, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.4 g of 2,2-dimethyl-3-formyl-4-bromo-6-cyano-3-chromene (m.p. 124°-125°; obtainable by dropwise addition of a solution of 2,2-dimethyl-5-cyano-5-chromanone in chloroform to a mixture of equal volume parts of DMF and PBr3 in chloroform and subsequent boiling for 11 hours), 0.9 g of 1H-2-pyridone, 3 g of K2CO3 and 20 ml of DMF is stirred at 60° for 1 hour. The mixture is diluted with ethyl acetate and filtered, and customary working up of the filtrate gives 2,2-dimethyl-3-formyl-4-(1,2-dihydro-2-oxo-1-pyridyl)-6-cyano-3-chromene ("A") m.p. 190°-192° C.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-b6a45842e95c4a7db7d292ac6427d816
Source dataset
uspto-grants-1992_09
Patent number
US05143924

Reaction notes

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