Ethanol → HCID 136109128, compound

HRID 650515Notes

Reaction equation

HRID 650515 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])C=O.[NH2:19][C:20]1[CH:24]=[CH:23][NH:22][N:21]=1.[CH2:25](O)C>>[Br:9][C:10]1[CH:11]=[CH:12][C:15]([CH:25]2[C:2]3[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=3[NH:19][C:20]3=[CH:24][CH:23]=[N:22][N:21]23)=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 4

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418806HCID 178418806, compound

Product 1

HCID 136109128HCID 136109128, compoundYield 49%

Procedure

A solution of 1,3-cyclohexanedione(0.56 g, 5 mmol), 3-bromo-4-fluorobenzaldehyde(1.01 g, 5 mmol), and 3-aminopyrazole (0.41 g, 5 mmol) in ethanol (5 mL) was heated at reflux for 24 hours. After the reaction mixture was allowed to cool to ambient temperature, the volatiles were evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.9 g (49 %) of the title compound.

Workup

  1. temperatureat reflux for 24 hours
  2. customthe volatiles were evaporated at reduced pressure
  3. customthe resulting residue was chromatographed on silica gel
  4. washeluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record
ord-5ed99fe157df44c4a0a543f900c29c14
Source dataset
uspto-grants-2001_08
Patent number
US06274587B1

Reaction notes

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