3-Bromo-5-ethoxy-4-hydroxybenzaldehyde → HCID 67410908, compound

HRID 909388Notes

Reaction equation

HRID 909388 reaction equation
[CH3:1][C:2]([NH2:7])=[CH:3][N+:4]([O-:6])=[O:5].[CH2:8]([CH:11]1[CH2:16][C:15](=[O:17])[CH2:14][C:13](=O)[CH2:12]1)[CH2:9][CH3:10].[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:29][CH2:30][CH3:31])[C:27]=1[OH:28])[CH:23]=O>C(O)C>[Br:19][C:20]1[CH:21]=[C:22]([CH:23]2[C:14]3[C:15](=[O:17])[CH2:16][CH:11]([CH2:8][CH2:9][CH3:10])[CH2:12][C:13]=3[NH:7][C:2]([CH3:1])=[C:3]2[N+:4]([O-:6])=[O:5])[CH:25]=[C:26]([O:29][CH2:30][CH3:31])[C:27]=1[OH:28]

Participants

5

Reactant 3

HCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehydeHCID 27372245-Propylcyclohexane-1,3-dioneHCID 714047121-Nitroprop-1-en-2-amine

Product 1

HCID 67410908HCID 67410908, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-methyl-2-nitro-vinylamine (1 g), 5-propylcyclohexane-1,3-dione (1.61 g) and 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (2.57 g) in ethanol (50 ml) was stirred at reflux for 17 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane. A precipitate formed, which was collected by filtration. The solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent. Yield: 2.8 g. MS-ESI: [M+H]+=465.0/467.0

Workup

  1. temperatureat reflux for 17 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customA precipitate formed
  5. filtrationwhich was collected by filtration
  6. customThe solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent

Sources & evidence

ORD record
ord-6614b13ee94444c9a27fb18c52faee20
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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