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

HRID 1817804Notes

Reaction equation

HRID 1817804 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][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][C:18](=[O:28])[CH:17]=1.C(OCC)(=O)C#C>>[C:22]1([CH:20]2[CH2:21][C:16]3[NH:15][C:2](=[O:1])[CH:3]=[CH:8][C:17]=3[C:18](=[O:28])[CH2:19]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 12182Ethyl propiolateHCID 18499675-Oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrileHCID 122101053-Amino-5-phenyl-2-cyclohexen-1-one

Product 1

HCID 135724197-Phenyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Procedure

In analogy to (Pettit, G. R.; Fleming, W. C.; Paull, K. D. J. Org. Chem. 1968, 33 (3) 1089-1092), 3-amino-5-phenylcyclohex-2-en-1-one reacted with ethyl propiolate to give the title compound as a colorless solid.

Sources & evidence

ORD record
ord-b475202e142c4550a6b87b23fab6c49a
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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