1,2-Cyclohexanedione → HCID 67378120, compound

HRID 877455Notes

Reaction equation

HRID 877455 reaction equation
Cl.[NH:2]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)N.[CH2:12]1[CH2:19][C:17](=O)[C:15](=[O:16])[CH2:14][CH2:13]1>CO.CC(O)=O.Cl>[O:16]=[C:15]1[C:14]2[NH:2][C:4]3[C:11](=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=3)[C:13]=2[CH2:12][CH2:19][CH2:17]1

Participants

6

Reactant 2

HCID 130061,2-CyclohexanedioneHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 67378120HCID 67378120, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Hydrazinylbenzonitrile hydrochloride (3 g, 17.6 mmol) dissolved in MeOH (30 mL), was heated to 60° C., and 1,2-cyclo hexadione (1.98 g, 17.6 mmol) in AcOH (30 mL) and HCl (12 mL) were added while maintaining the temperature at 60° C. The reaction mixture was stirred at 60° C. for 12 h and then cooled to room temperature. The volatiles were removed in vacuo and the residue was diluted with water, neutralized with saturated NaHCO3 solution and extracted with EtOAc (2×40 mL). The combined organic extracts were concentrated under reduced pressure to give the crude product which was purified by silica gel chromatography [EtOAc-hexane (1:3) as eluant] to provide the title compound (3.3 g, 89%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.80 (bs, 1H), 7.80 (d, J=2.0 Hz, 1H), 7.45 (dd, J=12.0, 2.0 Hz, 1H), 7.30 (d, J=12.5 Hz, 1H), 2.90 (t, J=9.0 Hz, 2H), 2.62 (t, J=9.0 Hz, 2H), 2.25 (m, 2H).

Workup

  1. temperaturewhile maintaining the temperature at 60° C
  2. temperaturecooled to room temperature
  3. customThe volatiles were removed in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with EtOAc (2×40 mL)
  6. concentrationThe combined organic extracts were concentrated under reduced pressure
  7. customto give the crude product which
  8. customwas purified by silica gel chromatography [EtOAc-hexane (1:3) as eluant]

Sources & evidence

ORD record
ord-c777f2e43dbd43d3bce2ba05159cf37c
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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