Cyclohexanone → HCID 19808730, compound

HRID 373993Notes

Reaction equation

HRID 373993 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:12][C:11]=1[NH:24]N>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[Cl:9][C:10]1[C:11]2[NH:24][C:2]3[CH2:3][CH2:4][CH2:5][CH2:6][C:1]=3[C:12]=2[C:13]([C:20]([O:22][CH3:23])=[O:21])=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:15]=1

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 67894734HCID 67894734, compound

Product 1

HCID 19808730HCID 19808730, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

To 10 ml of acetic acid were added 320 mg of cyclohexanone, 500 mg of zinc chloride and 800 mg of 2-chloro-4,5-bis(methoxycarbonyl)phenylhydrazine hydrochloride. The mixture was refluxed for 6 hours. Then, acetic acid was removed by distillation under reduced pressure. The residue was dissolved in 100 ml of ethyl acetate. The solution was washed with 1 N hydrochloric acid, an aqueous saturated sodium chloride solution and an aqueous saturated sodium hydrogen-carbonate solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/0 to 40/1) to obtain 270 mg (yield: 31%) of dimethyl 1-chloro-5,6,7,8-tetrahydrocarbazole-3,4-dicarboxylate as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customThen, acetic acid was removed by distillation under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  4. washThe solution was washed with 1 N hydrochloric acid
  5. dry with materialan aqueous saturated sodium chloride solution and an aqueous saturated sodium hydrogen-carbonate solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/0 to 40/1)

Sources & evidence

ORD record
ord-eb598d65f3874019acf905b61976cf37
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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