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

HRID 1986968Notes

Reaction equation

HRID 1986968 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[C:11](OCC)(=[O:14])[C:12]#[CH:13]>>[CH3:8][C:6]1([CH3:9])[CH2:7][C:2]2[NH:1][C:11](=[O:14])[CH:12]=[CH:13][C:3]=2[C:4](=[O:10])[CH2:5]1

Participants

3

Reactant 2

HCID 12182Ethyl propiolateHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-one

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-1abfd50883e64c89a7fe6ccee8f4c631
Source dataset
uspto-grants-2009_06
Patent number
US07550482B2

Reaction notes

Loading…