Water → 4-chloro-N-amino-phthalimide

HRID 37334Notes

Reaction equation

HRID 37334 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.O.[NH2:14]N.O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([NH2:14])[C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 2312394-Chloro-phthalimide

Product 1

HCID 193792274-chloro-N-amino-phthalimideYield 20.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cooled mixture of 1.81 g (10 mmol) 4-chloro phthalimide in 20 mL ethanol (96%) was added 0.5 mL (10 mmol) hydrazine monohydrate. The reaction mixture was stirred for 2 min. at room temperature and 2 min. at reflux. By adding 50 mL cold water pale yellow crystals formed after 1 h. Resulting crystals was filtered and recrystallized from ethanol to give 0.4 g (20%)4-chloro-N-amino-phthalimide :top 172°-175° C.; 1H NMR (200 MHz, DMSO-d6) d 4.90 (s, 2H, NH2), 7.82-7.92 (m, 3H, C6H3); it solidifies after melting and melts again around 345° C.

Workup

  1. temperatureat reflux
  2. customformed after 1 h
  3. customResulting crystals
  4. filtrationwas filtered
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ca901d6c476c4be7b70a5176f7913521
Source dataset
uspto-grants-1995_05
Patent number
US05420234

Reaction notes

Loading…