5-Propylcyclohexane-1,3-dione → 3-Bromo-5-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-2-(3-methoxy-benzyloxy)-benzoic acid methyl ester

HRID 1663381Notes

Reaction equation

HRID 1663381 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]=O)[CH:7]=[C:6]([Br:12])[C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1.[CH3:24]/[C:25](/[NH2:29])=[CH:26]\[C:27]#[N:28].[CH2:30]([CH:33]1[CH2:38][C:37](=[O:39])[CH2:36][C:35](=O)[CH2:34]1)[CH2:31][CH3:32]>C(O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]2[C:36]3[C:37](=[O:39])[CH2:38][CH:33]([CH2:30][CH2:31][CH3:32])[CH2:34][C:35]=3[NH:29][C:25]([CH3:24])=[C:26]2[C:27]#[N:28])[CH:7]=[C:6]([Br:12])[C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1

Participants

5

Reactant 3

HCID 27372245-Propylcyclohexane-1,3-dioneHCID 53247203-AminocrotonitrileHCID 87399760HCID 87399760, compound

Product 1

HCID 674350333-Bromo-5-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-2-(3-methoxy-benzyloxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-5-formyl-2-(3-methoxy-benzyloxy)-benzoic acid methyl ester (3.78 g), 3-aminocrotonitrile (822 mg) and 5-propylcyclohexane-1,3-dione (1535 mg) in ethanol (25 ml) was stirred at 80° C. for 17 h. The mixture was concentrated in vacuo.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3811951a560c485eaa3826507e8e39ee
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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