Phenylhydrazine hydrochloride → HCID 13491214, compound

HRID 1664485Notes

Reaction equation

HRID 1664485 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Cl.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCO>[CH2:7]1[C:2]2[NH:18][C:12]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:3]=2[CH2:4][CH:5]([C:8]([OH:10])=[O:9])[CH2:6]1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 1927304-Oxocyclohexanecarboxylic acid

Product 1

HCID 13491214HCID 13491214, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-oxo-cyclohexanecarboxylic acid (4.05 g, 28.5 mmol) and phenylhydrazine hydrochloride (4.12 g, 28.5 mmol) in EtOH (200 ml) is stirred at reflux for 3 h. Then, the solvent is evaporated and the residue is dissolved in boiling toluene. Precipitating ammonium chloride is filtered off and the clear filtrate is cooled to rt. The resulting precipitate is filtered and tried under high vacuum to give pure subtitle compound as a white solid (5.16 g) in 84% yield. tR (LC-3) 2.21 min; ESI-MS (positive ion): m/z 216.30 [M+H]+(calcd 215.09 for C13H13NO2). 1H-NMR (CDCl3): 2.01 (m, 1H); 2.28 (m, 1H); 2.83 (m, 4H); 3.04 (dd, J=14.8 Hz, 4.7 Hz, 1H); 7.02 (m, 2H); 7.19 (d, J=7.2 Hz, 1H); 7.38 (d, J=7.0 Hz, 1H); 7.63 (s br, 1H).

Workup

  1. temperatureat reflux for 3 h
  2. customThen, the solvent is evaporated
  3. dissolutionthe residue is dissolved
  4. filtrationPrecipitating ammonium chloride is filtered off
  5. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-0956b022d45f482b821916118ed058ba
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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