Phenylhydrazine hydrochloride → HCID 67358882, compound

HRID 1664492Notes

Reaction equation

HRID 1664492 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].Cl.[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C>[C:1]([CH:3]1[CH2:8][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:17][C:6]=2[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 122356394-Oxocyclohexane-1-carbonitrile

Product 1

HCID 67358882HCID 67358882, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-cyano-cyclohexanone (0.48 g, 3.9 mmol) and phenylhydrazine hydrochloride (0.42 g, 3.9 mmol) in glacial acetic acid (5 ml) is stirred at reflux for 1 h. The solvent is evaporated and the residue chromatographed on silica gel (heptane/EtOAc 2:1) to deliver the title compound as a brownish solid (158 mg) in 50% yield. tR (LC-5) 0.91 min; ESI-MS (positive ion): m/z 197.10 [M+H]+ (calcd 196.25 for C13H12N2). 1H-NMR (CDCl3): 2.25 (m, 2H); 2.96 (m, 5H); 7.14 (m, 2H); 7.30 (d, J=7.7 Hz, 1H); 7.45 (d, J=7.1 Hz, 1H); 7.79 (br s, 1H).

Workup

  1. temperatureat reflux for 1 h
  2. customThe solvent is evaporated
  3. customthe residue chromatographed on silica gel (heptane/EtOAc 2:1)
  4. custom0.91 min

Sources & evidence

ORD record
ord-2d30e0d532f7426b8d952a4933d7db29
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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