Ethanol → HCID 131729092, compound

HRID 1670716Notes

Reaction equation

HRID 1670716 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:25][CH3:26])[C:23]=1[OH:24])C=O.[CH3:27]/[C:28](/[NH2:32])=[CH:29]\[C:30]#[N:31].[CH2:33](O)C>>[Br:15][C:16]1[CH:17]=[C:18]([N:32]2[C:9]3[CH2:8][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:12][C:11](=[O:13])[C:10]=3[CH2:33][C:29]([C:30]#[N:31])=[C:28]2[CH3:27])[CH:21]=[C:22]([O:25][CH3:26])[C:23]=1[OH:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 180995-BromovanillinHCID 5689621,3-Cyclohexanedione, 5-phenyl-HCID 53247203-Aminocrotonitrile

Product 1

HCID 131729092HCID 131729092, compound

Conditions

Temperature
75 °C

Procedure

A mixture of 5-phenylcyclohexane-1,3-dione (0.51 g), 3-bromo-5-methoxy-4-hydroxybenzaldehyde (0.62 g) and 3-aminocrotonitrile (0.22 g) in 20 mL absolute ethanol was stirred at 75° C. for 3 h. The reaction mixture was concentrated and the title compound was obtained as a off-white solid after flash column chromatography (silica gel, heptane/ethyl acetate (3/7, v/v), Rf=0.36).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6985c955959d474195b7fa89898c4e8e
Source dataset
uspto-grants-2011_08
Patent number
US07994189B2

Reaction notes

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