Hydrazine hydrate (1:1) → 4-Phenyl-1-(2H)-phthalazinone

HRID 44435Notes

Reaction equation

HRID 44435 reaction equation
C[N:2](C)[NH:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.NN.O>>[C:12]1([C:11]2[C:6]3[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:4](=[O:19])[NH:3][N:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90925702-Benzoyl-benzoic acid N',N'-dimethyl-hydrazide

Product 1

HCID 2191504-Phenyl-1-(2H)-phthalazinoneYield 95%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-benzoyl-benzoic acid N′,N′-dimethyl-hydrazide 17 (1 mmol) and H2NNH2.H2O (18 mmol) was stirred for 2 hrs at 100° C. After the excess hydrazine was removed under reduced pressure, the crude product was purified by chromatography on silica gel ((1:2) EtOAc:hexane) to give the desired product in 95% yield.

Workup

  1. customAfter the excess hydrazine was removed under reduced pressure
  2. customthe crude product was purified by chromatography on silica gel ((1:2) EtOAc:hexane)

Sources & evidence

ORD record
ord-1ab645950f3d47b0bb02ad4fe222c51a
Source dataset
uspto-grants-2013_09
Patent number
US08541428B2

Reaction notes

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