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

HRID 1663367Notes

Reaction equation

HRID 1663367 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

Procedure

A mixture of 3-bromo-4-hydroxy-5-nitro-benzaldehyde (2 g), 3-aminocrotonitrile (667 mg) and 5-propylcyclohexane-1,3-dione (1.25 g) in ethanol (75 ml) was heated to reflux for 17 h. The mixture was concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 17 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-76a27bf88529460d9d013dd0221cab81
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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