Phthalide → 2-(hydroxymethyl)-N'-phenylbenzohydrazide

HRID 2291807Notes

Reaction equation

HRID 2291807 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][O:11]1)=[O:10]>CCOCC>[OH:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=1[C:9]([NH:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10]

Participants

4

Reactant 2

HCID 6885PhthalideHCID 7516Phenylhydrazine

Product 1

HCID 12072532-(hydroxymethyl)-N'-phenylbenzohydrazide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

The method adopted is disclosed in Wislicenus (Berichte 20 401). Phenyl hydrazine (27 ml) and phthalide (33 g) were heated together at 70° to 80° C. for 3 hours. After cooling to 20° C. the solid product was stirred with ether (100 ml) and the product collected by filtration, washed with ether and recrystallised from 2-propanol. Yield 9.6 g (16%) melting point 170°-172° C.

Workup

  1. filtrationthe product collected by filtration
  2. washwashed with ether
  3. customrecrystallised from 2-propanol

Sources & evidence

ORD record
ord-4f47a108ee8445f8a513833621736870
Source dataset
uspto-grants-1989_01
Patent number
US04798780

Reaction notes

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