5-Propylcyclohexane-1,3-dione → 4-[3-Bromo-4-(3-methoxy-benzyloxy)-5-nitro-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

HRID 1663363Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:20]([O-:22])=[O:21])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH:5]=O.[CH3:23]/[C:24](/[NH2:28])=[CH:25]\[C:26]#[N:27].[CH2:29]([CH:32]1[CH2:37][C:36](=[O:38])[CH2:35][C:34](=O)[CH2:33]1)[CH2:30][CH3:31]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:35]3[C:36](=[O:38])[CH2:37][CH:32]([CH2:29][CH2:30][CH3:31])[CH2:33][C:34]=3[NH:28][C:24]([CH3:23])=[C:25]2[C:26]#[N:27])[CH:7]=[C:8]([N+:20]([O-:22])=[O:21])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-bromo-4-(3-methoxy-benzyloxy)-5-nitro-benzaldehyde (50 mg), 3-aminocrotonitrile (13 mg) and 5-propylcyclohexane-1,3-dione (25 mg) in 10 ml of ethanol was stirred at 80° C. for 17 h. The mixture was concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 8/2→1/1 (v/v) as eluent.

Workup

concentrationThe mixture was concentrated in vacuo
customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 8/2→1/1 (v/v) as eluent

Sources & evidence

ORD record: ord-9c6cb09aada94387b3abdea5423bd469
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034945B2

Reaction notes

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