HCID 67339927, compound → HCID 67340581, compound

HRID 2092347Notes

Reaction equation

HRID 2092347 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[CH:5]2>CCO.[Pd]>[NH2:13][C:3]1[C:2]([CH3:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[N:6][NH:7][C:8]2=[O:12]

Participants

4

Reactant 1

HCID 67339927HCID 67339927, compound

Product 1

HCID 67340581HCID 67340581, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 6-methyl-5-nitrophthalazin-1(2H)-one (9.446 g, 46 mmol) in EtOH (1000 ml) charged to a 2000 mL round bottom flask, palladium, 10 wt. % on activated carbon (0.490 g, 0.46 mmol) was added. The reaction mixture was stirred at 50° C. for 6 days under H2 (1 atm). When complete, the reaction mixture was filtered through a small pad of celite, washing with excess EtOH and some DMF. The liquid was then concentrated under vacuum to give 5-amino-6-methylphthalazin-1(2H)-one (7.99 g, 99% yield) as a yellow solid. MS (M+H)+ 176.

Workup

  1. additioncharged to a 2000 mL round bottom flask
  2. filtrationWhen complete, the reaction mixture was filtered through a small pad of celite
  3. washwashing with excess EtOH
  4. concentrationThe liquid was then concentrated under vacuum

Sources & evidence

ORD record
ord-bd5e7a59d4274b8ca4b5e2904d9d2fa9
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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