Ethyl propiolate → 7,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

HRID 1817798Notes

Reaction equation

HRID 1817798 reaction equation
[O:1]=[C:2]1CCC[C:8]2NC(=S)C(C#N)=C[C:3]1=2.[NH2:15][C:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18](=[O:24])[CH:17]=1.C(OCC)(=O)C#C>>[CH3:22][C:20]1([CH3:23])[CH2:21][C:16]2[NH:15][C:2](=[O:1])[CH:3]=[CH:8][C:17]=2[C:18](=[O:24])[CH2:19]1

Participants

4

Reactant 3

HCID 12182Ethyl propiolateHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 18499675-Oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

Product 1

HCID 135163797,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dioneYield 78.5%

Procedure

In analogy to (Pettit, G. R.; Fleming, W. C.; Paull, K. D. J. Org. Chem. 1968, 33 (3) 1089-1092), 3-amino-5,5-dimethylcyclohex-2-en-1-one was reacted with ethyl propio-late to give the title compound as a light brown solid in 78.5% yield.

Sources & evidence

ORD record
ord-43529e555611496dbaf7d858aba485d9
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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