1,2-Cyclohexanedione → HCID 67378017, compound

HRID 877468Notes

Reaction equation

HRID 877468 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[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>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]2[C:5]=1[C:13]1[CH2:12][CH2:19][CH2:17][C:15](=[O:16])[C:14]=1[NH:10]2

Participants

4

Reactant 2

HCID 130061,2-CyclohexanedioneHCID 3084937(2,5-Dichlorophenyl)hydrazine monohydrochloride

Product 1

HCID 67378017HCID 67378017, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(2,5-Dichlorophenyl)hydrazine hydrochloride (0.3 g, 1.40 mmol) was dissolved in MeOH (3 mL) and 1,2-cyclo hexadione (0.15 g, 1.40 mmol) was added and the mixture heated to 60° C. for 24 h. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The residue was diluted with water, neutralized with NaHCO3 solution and extracted with EtOAc (3×15 mL). The combined organic extracts were concentrated in vacuo to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant] to provide the title compound (0.35 g, 11.8%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.92 (bs, 1H), 7.26 (d, J=8.2 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 3.36 (t, J=6.2 Hz, 2H), 2.69 (t, J=6.0 Hz, 2H), 2.34-2.21 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe volatiles were removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc (3×15 mL)
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customto give the crude compound which
  7. customwas purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-2165e8e3a3f74a0db088aa7960597654
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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