Hydrazine hydrate (1:1) → HCID 57214671, compound

HRID 2092346Notes

Reaction equation

HRID 2092346 reaction equation
C([N:5]1[CH:13](O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:15])[CH:11]=2)[C:6]1=[O:16])(C)(C)C.O.[NH2:18]N>CC(O)=O.O>[CH3:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:16])[NH:18][N:5]=[CH:13]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67338907HCID 67338907, compound

Product 1

HCID 57214671HCID 57214671, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-tert-butyl-3-hydroxy-5-methylisoindolin-1-one (10.54 g, 48.1 mmol) in AcOH (250 ml) charged to a 500 mL round bottom and stirred at 80° C., hydrazine hydrate (3.51 ml, 72.1 mmol) was added. The reaction mixture was stirred at 80° C. for 90 min. The reaction mixture was then cooled and diluted with water and extracted with 4 L DCM. The organics were washed with brine, dried over magnesium sulfate and concentrated under vacuum to give 6-methylphthalazin-1(2H)-one. MS (M+H)+ 161.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 90 min
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with 4 L DCM
  4. washThe organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5070da5adf0340d4a0b5a28af8d38cc0
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

Loading…