5-Propylcyclohexane-1,3-dione → HCID 67436163, compound

HRID 1663379Notes

Reaction equation

HRID 1663379 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH:10]=O)[CH:7]=[C:6]([Br:12])[C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1.[CH3:25]/[C:26](/[NH2:30])=[CH:27]\[C:28]#[N:29].[CH2:31]([CH:34]1[CH2:39][C:38](=[O:40])[CH2:37][C:36](=O)[CH2:35]1)[CH2:32][CH3:33]>C(O)C>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH:10]2[C:37]3[C:38](=[O:40])[CH2:39][CH:34]([CH2:31][CH2:32][CH3:33])[CH2:35][C:36]=3[NH:30][C:26]([CH3:25])=[C:27]2[C:28]#[N:29])[CH:7]=[C:6]([Br:12])[C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1

Participants

5

Reactant 3

HCID 27372245-Propylcyclohexane-1,3-dioneHCID 53247203-AminocrotonitrileHCID 86625160HCID 86625160, compound

Product 1

HCID 67436163HCID 67436163, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-5-formyl-2-(3-nitro-benzyloxy)-benzoic acid methyl ester (788 mg), 3-aminocrotonitrile (165 mg) and 5-propylcyclohexane-1,3-dione (308 mg) in ethanol (5 ml) was heated at 80° C. for 17 h. The mixture was concentrated in vacuo. The residue was purified by preparative HPLC (Method B).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by preparative HPLC (Method B)

Sources & evidence

ORD record
ord-2bf235e8a202415d812bd6bf8bfb48d4
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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