1,2-Cyclohexanedione → HCID 67377466, compound

HRID 877475Notes

Reaction equation

HRID 877475 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[NH:10]N.[CH2:12]1[CH2:19][C:17](=O)[C:15](=[O:16])[CH2:14][CH2:13]1>CO.CC(O)=O.Cl>[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]2[C:4]=1[NH:10][C:14]1[C:15](=[O:16])[CH2:17][CH2:19][CH2:12][C:13]2=1

Participants

6

Reactant 2

HCID 130061,2-CyclohexanedioneHCID 247210492-Chloro-4-fluorophenylhydrazine hydrochloride

Product 1

HCID 67377466HCID 67377466, compoundYield 56.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 2-chloro-4-fluoro phenyl hydrazine hydrochloride (0.3 g, 1.5 mmol) in MeOH (2.5 mL), a solution of 1,2-cyclohexadione (0.17 g, 1.5 mmol) in AcOH (2.5 mL) and conc. HCl (1 mL) were added. The resulting mixture was stirred at 60° C. for 12 h, then cooled to room temperature and MeOH was removed in vacuo. Water (25 mL) was added and the reaction mixture was basified with NaHCO3 (pH 8). The crude residue was extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (50 mL), dried over Na2SO4 and concentrated in vacuo to give the crude material which was purified by silica gel chromatography [EtOAc-hexane (1:19) as eluant] to afford the title compound (0.2 g, 55%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.84 (bs, 1H), 7.26-7.17 (m, 2H), 2.99-2.93 (t, J=6.0 Hz, 2H), 2.70-2.64 (q, J=7.4, 5.8 Hz, 2H), 2.34-2.21 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. customMeOH was removed in vacuo
  3. additionWater (25 mL) was added
  4. extractionThe crude residue was extracted with EtOAc (2×30 mL)
  5. washThe combined organic extracts were washed with water (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the crude material which
  9. customwas purified by silica gel chromatography [EtOAc-hexane (1:19) as eluant]

Sources & evidence

ORD record
ord-726e0f9208c94921abcd92a94f5bffc7
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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