Hydrazine → HCID 19973161, compound

HRID 22393Notes

Reaction equation

HRID 22393 reaction equation
[C:1]1([C:7]2[N:8]([N:12]3C(=O)C4C(=CC=CC=4)C3=O)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>C(O)C>[C:1]1([C:7]2[N:8]([NH2:12])[CH:9]=[CH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 19973165HCID 19973165, compound

Product 1

HCID 19973161HCID 19973161, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension consisting of 2-(2-phenyl-1H-pyrrol-1-yl)-1H-isoindol-1,3(2H)dione (7.2 g) in abs. ethanol (150 ml) was added hydrazine (3.9 ml) at room temperature. The reaction mixture was warmed to reflux for 2 hours and allowed to cool to room temperature overnight. The solid by-product was filtered and washed with ether. The combined filtrates were concentrated in vacuo to give an oil which solidified on standing. Recrystallization from ether afforded 3.9 g of the product as a solid, m.p. 80°-82° C.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 2 hours
  3. filtrationThe solid by-product was filtered
  4. washwashed with ether
  5. concentrationThe combined filtrates were concentrated in vacuo
  6. customto give an oil which
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-da6c9253cbcc4821a66097db02bfb112
Source dataset
uspto-grants-1995_06
Patent number
US05428053

Reaction notes

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