Ethanol → HCID 86583963, compound

HRID 990829Notes

Reaction equation

HRID 990829 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH3:16])=[O:5].[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1.C(O)C>[Pd].O>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]([C:4](=[O:5])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[F:1])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:8]([CH3:16])[CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8079CyclohexeneHCID 40507012-Fluoro-N-(2-methyl-4-nitrophenyl)benzamide

Product 1

HCID 86583963HCID 86583963, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of 2-fluoro-N-(2-methyl-4-nitrophenyl)benzamide (4.55 g), cyclohexene (30 mL), ethanol (70 mL), water (30 mL) and 10% palladium on charcoal (3 g) is heated at reflux for 30 minutes. The mixture is filtered through diatomaceous earth and concentrated under reduced pressure. The resulting oil is dissolved in 50 mL of ethyl acetate and cooled at 4° C. for 12 hours. Filtration provides the product as a tan solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe mixture is filtered through diatomaceous earth
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting oil is dissolved in 50 mL of ethyl acetate
  6. filtrationFiltration

Sources & evidence

ORD record
ord-8fcb5f77509146f498fbf2c639e6624d
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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