5-Propylcyclohexane-1,3-dione → HCID 67434333, compound

HRID 1663374Notes

Reaction equation

HRID 1663374 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[Br:13].[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>[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]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:4][C:3]=1[Br:13]

Participants

5

Reactant 3

HCID 27372245-Propylcyclohexane-1,3-dioneHCID 53247203-AminocrotonitrileHCID 20244647HCID 20244647, compound

Product 1

HCID 67434333HCID 67434333, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-amino-3-bromo-5-nitro-benzaldehyde (665 mg), 3-aminocrotonitrile (223 mg), 5-propylcyclohexane-1,3-dione (418 mg) in 50 ml of ethanol was stirred at 80° C. for 4 h, then at room temperature for 16 h. The reaction 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. waitat room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. 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-7dd0052b105844de8452d681a6dfd578
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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