3-Bromo-4-hydroxy-5-nitrobenzaldehyde → HCID 67435380, compound

HRID 1663385Notes

Reaction equation

HRID 1663385 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.[CH3:14]/[C:15](/[NH2:19])=[CH:16]\[C:17]#[N:18].[CH2:20]([CH:23]1[CH2:28][C:27](=[O:29])[CH2:26][C:25](=O)[CH2:24]1)[CH2:21][CH3:22]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:26]3[C:27](=[O:29])[CH2:28][CH:23]([CH2:20][CH2:21][CH3:22])[CH2:24][C:25]=3[NH:19][C:15]([CH3:14])=[C:16]2[C:17]#[N:18])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 14943783-Bromo-4-hydroxy-5-nitrobenzaldehydeHCID 27372245-Propylcyclohexane-1,3-dioneHCID 53247203-Aminocrotonitrile

Product 1

HCID 67435380HCID 67435380, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-4-hydroxy-5-nitro-benzaldehyde (18.26 g), 3-aminocrotonitrile (6.09 g) and 5-propylcyclohexane-1,3-dione (11.45 g) in ethanol (250 ml) was stirred at 80° C. for 17 h. The mixture was concentrated in vacuo. The residue was purified by chromatography on silicagel in dichloromethane as eluent.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on silicagel in dichloromethane as eluent

Sources & evidence

ORD record
ord-5ded5b8bd1f84c27b4dbc561ba532673
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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