Ethanol → HCID 59641990, compound

HRID 1436214Notes

Reaction equation

HRID 1436214 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[NH:10]N.O=[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(O)C>C(O)(=O)C>[Br:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]2[C:4]=1[NH:10][C:13]1[CH:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][CH2:16][CH2:17][C:18]2=1

Participants

5

Reactant 3

HCID 702EthanolHCID 91229Ethyl 2-oxocyclohexylacetateHCID 16370085(2-Bromo-4-fluorophenyl)hydrazine hydrochloride

Product 1

HCID 59641990HCID 59641990, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 7.24 g of (2-bromo-4-fluorophenyl)hydrazine hydrochloric acid salt in 100 mL of acetic acid, 5.5 g of ethyl 2-(2-oxocyclohexyl)-acetate was added. The resulting mixture was heated to reflux for 1 h. Then 10 mL of ethanol was added and the reaction mixture was heated at reflux overnight. The solvent was evaporated and the residue was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution, water, and brine successively. The organic layer was separated and dried over anhydrous sodium sulfate, filtered, and evaporated. The residue was purified by flash chromatography over silica gel (5% EtOAc/hexane) to afford 3.12 g of desired compound.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 1 h
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux overnight
  6. customThe solvent was evaporated
  7. additionthe residue was diluted with EtOAc
  8. washwashed with saturated aqueous NaHCO3 solution, water, and brine successively
  9. customThe organic layer was separated
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was purified by flash chromatography over silica gel (5% EtOAc/hexane)

Sources & evidence

ORD record
ord-9884cc138a63427184262aefebccb436
Source dataset
uspto-grants-2009_11
Patent number
US07618994B2

Reaction notes

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