Phthalimide → 2,3-Dichloro-6-nitrobenzylamine

HRID 636363Notes

Reaction equation

HRID 636363 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(=O)[NH:11]C(=O)C2=CC=CC=C12.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([CH2:28]Cl)[C:20]=1[Cl:30]>>[Cl:30][C:20]1[C:19]([Cl:18])=[CH:24][CH:23]=[C:22]([N+:25]([O-:27])=[O:26])[C:21]=1[CH2:28][NH2:11]

Participants

4

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 98346632,3-Dichloro-6-nitrobenzyl chloride

Product 1

HCID 155242392,3-Dichloro-6-nitrobenzylamineYield 75%

Procedure

Potassium carbonate and 2 equivalents of phthalimide are ground together and heated to reflux with 2 equivalents of 1,2-dichloro-3-chloromethyl-4-nitrobenzene for three hours. Upon cooling, the substituted benzylphthalimide crystallizes and is filtered in 60-80% yield. 2,3-Dichloro-6-nitrobenzylamine is obtained in a 75-95% yield with acid hydrolysis using hydrochloric acid from the substituted benzylphthalimide.

Workup

  1. temperatureheated
  2. temperatureUpon cooling
  3. customthe substituted benzylphthalimide crystallizes
  4. filtrationis filtered in 60-80% yield

Sources & evidence

ORD record
ord-509bd385bf93474ba5bc09727ef0d5db
Source dataset
uspto-grants-2001_02
Patent number
US06194420B1

Reaction notes

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