Hydrazine → 4-(4-methoxybenzyl)phthalazin-1(2H)-one

HRID 911119Notes

Reaction equation

HRID 911119 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([NH:16]C)=[O:15])=O)=[CH:5][CH:4]=1.[NH2:22]N>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:12]3[C:13](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14](=[O:15])[NH:16][N:22]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 667315312-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide

Product 1

HCID 123328504-(4-methoxybenzyl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide (1.76 g, 6.20 mmol) in EtOH (20 mL) was added hydrazine (3.50 ml, 112 mmol). A water condenser was attached and the mixture was heated to reflux under a nitrogen atmosphere for 5 days. After concentration, the reaction was diluted with EtOAc and extracted with water. The organics were dried over sodium sulfate, filtered and concentrated. The crude was purified by washing the resulting solid with diethyl ether and filtering to yield 4-(4-methoxybenzyl)phthalazin-1(2H)-one as a white solid. MS m/z=267[M+1]+. Calc'd for C16H14N2O2: 266.30.

Workup

  1. customA water condenser was attached
  2. temperaturethe mixture was heated
  3. temperatureto reflux under a nitrogen atmosphere for 5 days
  4. concentrationAfter concentration
  5. additionthe reaction was diluted with EtOAc
  6. extractionextracted with water
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified
  11. washby washing the resulting solid with diethyl ether
  12. filtrationfiltering

Sources & evidence

ORD record
ord-6a761fe7acb74137adaf295429d748d9
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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