Ethyl 2-oxocyclohexylacetate → 2-(4-chloro-2-fluorophenyl)-4,4a,5,6,7,8-hexahydro-3(2H)-cinnolinone

HRID 258495

Reaction equation

HRID 258495 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[C:4]([F:10])[CH:3]=1.CC[O:13][C:14]([CH2:16][CH:17]1[C:22](=O)[CH2:21][CH2:20][CH2:19][CH2:18]1)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:13])[CH2:16][CH:17]3[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)=[N:9]2)=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 2

HCID 91229Ethyl 2-oxocyclohexylacetateHCID 2782934(4-Chloro-2-fluorophenyl)hydrazine

Product 1

HCID 214257252-(4-chloro-2-fluorophenyl)-4,4a,5,6,7,8-hexahydro-3(2H)-cinnolinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.0 Parts of 4-chloro-2-fluorophenylhydrazine and 9.2 parts of ethyl 2-cyclohexanoneacetate [bp 92°-93°, 0.5 mm Hg; prepared by the method described by A. Sergre, et al., J. Amer. Chem. Soc., 79 3503 (1957)] were dissolved in 75 parts of glacial acetic acid, and the resulting solution was refluxed for 16 hours. The reaction solvent was removed under a reduced pressure of 300 mm Hg, and the residual brown oil was dissolved in 150 parts of methylene chloride. The organic solution was washed with saturated aqueous sodium bicarbonate solution, dried with anhydrous magnesium sulfate and the solvent was removed under a reduced pressure of 300 mm Hg to give 2-(4-chloro-2-fluorophenyl)-4,4a,5,6,7,8-hexahydro-3(2H)-cinnolinone as a brown oil that solidified on scratching. Purification was achieved by recrystallization from cyclohexane to yield 5.9 parts of tan solid, mp 110°-112°.

Workup

  1. customprepared by the method
  2. temperaturethe resulting solution was refluxed for 16 hours
  3. customThe reaction solvent was removed under a reduced pressure of 300 mm Hg
  4. dissolutionthe residual brown oil was dissolved in 150 parts of methylene chloride
  5. washThe organic solution was washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customthe solvent was removed under a reduced pressure of 300 mm Hg

Sources & evidence

ORD record
ord-f101a851078940ca9c3c4673960a008a
Source dataset
uspto-grants-1977_07
Patent number
US04033751

Linked notes

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