Hydrazine hydrate (1:1) → 4-(3,4-Dimethoxy-phenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

HRID 1919524Notes

Reaction equation

HRID 1919524 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:6]([CH:8]1[CH:13]([C:14](O)=[O:15])[CH2:12][CH:11]=[CH:10][CH2:9]1)=O.O.[NH2:23][NH2:24]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[CH:8]3[CH:13]([CH2:12][CH:11]=[CH:10][CH2:9]3)[C:14](=[O:15])[NH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 222196226-(3,4-Dimethoxy-benzoyl)-cyclohex-3-enecarboxylic acid

Product 1

HCID 223371824-(3,4-Dimethoxy-phenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(3,4-dimethoxy-benzoyl)-cyclohex-3-enecarboxylic acid (112 mg, 0.39 mmol, 1.0 eq) and hydrazine hydrate (31 mg, 0.96 mmol, 2.5 eq) in EtOH (3 mL) was refluxed for 4 hr. The reaction was then cooled to room temperature and then concentrated under reduced pressure to oil. The oil was dissolved in EtOAc and washed with water followed by brine. The organic layer was then dried over Na2SO4, filtered through paper, and concentrated under reduced pressure to oil. The product was recrystallized in EtOH to yield a white solid.

Workup

  1. temperaturewas refluxed for 4 hr
  2. concentrationconcentrated under reduced pressure to oil
  3. dissolutionThe oil was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. filtrationfiltered through paper
  7. concentrationconcentrated under reduced pressure to oil
  8. customThe product was recrystallized in EtOH
  9. customto yield a white solid

Sources & evidence

ORD record
ord-899a43dff08b4dcb9e20254a2ca96e05
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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