Cyclohexanone → HCID 5324600, compound

HRID 659649Notes

Reaction equation

HRID 659649 reaction equation
[NH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])N.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CC(O)=O>[C:4]1([C:5]([O:7][CH3:8])=[O:6])[C:3]2[NH:1][C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 11805118HCID 11805118, compound

Product 1

HCID 5324600HCID 5324600, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A 150-mL round-bottom flask was placed a solution of methyl 2-hydrazinylbenzoate (7.81 g, 1.00 equiv, 1%) in AcOH (70 mL). To this solution was added cyclohexanone (4.5 g, 45.92 mmol, 1.00 equiv) dropwise with stirring at 80° C. The resulting solution was heated to reflux for 2 hr in an oil bath. Upon completion, the reaction was then quenched with water (50 mL). The solids were collected by filtration and washed with H2O (2×50 mL) affording methyl 6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate as white solid (6 g, 55.8%).

Workup

  1. customA 150-mL round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 2 hr in an oil bath
  4. customUpon completion, the reaction was then quenched with water (50 mL)
  5. filtrationThe solids were collected by filtration
  6. washwashed with H2O (2×50 mL)

Sources & evidence

ORD record
ord-da46af79dc554475a01c4f6c7264aee4
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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