Sulfuric Acid → HCID 67377568, compound

HRID 877502Notes

Reaction equation

HRID 877502 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N=C2CCCCC2=O)=[C:4]([F:17])[CH:3]=1.OS(O)(=O)=O.[C:23]([O-:26])(O)=O.[Na+]>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([F:17])[CH:3]=1)[NH:8][C:7]1[C:23](=[O:26])[CH2:5][CH2:4][CH2:3][C:2]2=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86676830HCID 86676830, compound

Product 1

HCID 67377568HCID 67377568, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2-(4-chloro-2-fluorophenyl)hydrazono)cyclohexanone (0.5 g, 1.9 mmol) in MeCN (5 mL), H2SO4 (0.31 mL, 5.9 mmol, 1.8M solution) was added slowly and the resulting mixture was heated to 80° C. for 12 h. The reaction mixture was cooled to room temperature, basified with saturated NaHCO3 (pH-8) and extracted with EtOAc (2×30 mL). The combined organic extracts were dried over sodium Na2SO4 and concentrated in vacuo to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant] to provide the title compound (120 mg, 25%). 1H NMR (200 MHz, CDCl3, δ in ppm): 8.96 (bs, 1H), 7.43 (d, J=1.0 Hz, 1H), 7.12 (dd, 1H, J=10.2, 1.60 Hz, 1H), 2.99 (t, J=5.8 Hz, 2H), 2.71 (t, J=6.0 Hz, 2H), 2.34-2.21 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over sodium Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound which
  6. customwas purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-27cc1a5fcbc5431da1da42bb7e6391e4
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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