Phthalide → HCID 15702298, compound

HRID 1087708Notes

Reaction equation

HRID 1087708 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]1([C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1)=[O:13]>C(#N)C>[OH:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[C:12]([NH:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:13]

Participants

4

Reactant 2

HCID 6885PhthalideHCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 15702298HCID 15702298, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

41.3 g of 4-nitrophenylhydrazine and 33 g of phthalide were dissolved in 330 ml of acetonitrile. The solution was heated under reflux with stirring over 4 hours. The reaction solution was allowed to stand for cooling to room temperature. The resulting solid was then filtered off, and recrystallized from acetonitrile to obtain 15.1 g of 1-(2'-hydroxymethylbenzoyl)-2-(4-nitrophenyl) hydrazine (yield of 21.0%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. filtrationThe resulting solid was then filtered off
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-67f4652cafa746fba160a73c0d38e0f1
Source dataset
uspto-grants-1990_10
Patent number
US04960672

Reaction notes

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