4-Oxocyclohexanecarboxylic acid → HCID 67359980, compound

HRID 1664487Notes

Reaction equation

HRID 1664487 reaction equation
Cl.[C:2]1([N:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:17]1[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]1>CC(O)=O>[CH2:14]([O:13][C:11]([CH2:10][N:8]1[C:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][C:18]=2[C:7]2[C:2]1=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 1927304-Oxocyclohexanecarboxylic acidHCID 85664360HCID 85664360, compound

Product 1

HCID 67359980HCID 67359980, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl (N-phenyl-hydrazino)-acetate hydrochloric acid salt (2.3 g, 10 mmol) and 4-oxo-cyclohexanecarboxylic acid (1.42 g, 10 mmol) in glacial AcOH (20 ml) is stirred at 70° C. for 1 h. The suspension is allowed to cool to rt, poured onto H2O and stirred for 1 h. The resulting precipitate is filtered, washed with H2O and dried under high vacuum to give pure 9-ethoxycarbonylmethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid as a white solid (2.85 g) in 93% yield.

Workup

  1. temperatureto cool to rt
  2. additionpoured onto H2O
  3. stirringstirred for 1 h
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with H2O
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-ea3e57f591dc4e5592a0ac3dbbca175a
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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