Hydrazine hydrate (1:1) → Pyrazolo(5,1-a)isoquinolin-5(6H)-one, 2-phenyl-

HRID 579939Notes

Reaction equation

HRID 579939 reaction equation
O=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([OH:21])=O)[CH2:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.[NH2:23][NH2:24]>C(O)C>[C:5]1([C:4]2[CH:3]=[C:2]3[C:12]4[C:13]([CH2:18][C:19](=[O:21])[N:24]3[N:23]=2)=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 184426Benzeneacetic acid, 2-(1,3-dioxo-3-phenylpropyl)-

Product 1

HCID 184416Pyrazolo(5,1-a)isoquinolin-5(6H)-one, 2-phenyl-Yield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (10 ml), there were added 2-(1,3-dioxo-3-phenylpropyl) phenylacetic acid (1.42 g) and hydrazine hydrate (0.25 g), followed by heating under reflux for 2 hours. Thereafter, the reaction mixture was cooled to give 2-phenyl-5,6-dihydropyrazolo-[5,1-a]isoquinolin-5-one (1.06 g). Mp. 181°-183° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. temperatureThereafter, the reaction mixture was cooled

Sources & evidence

ORD record
ord-ce309ac7754b4e49a5beab5f8053156c
Source dataset
uspto-grants-1988_06
Patent number
US04751226

Reaction notes

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