Acetic Acid → 4-(3-Amino-4-chlorobenzyl)amino-6-chloroquinazoline

HRID 1900669Notes

Reaction equation

HRID 1900669 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[N+:21]([O-])=O.C(O)(=O)C>[Fe].C(O)C>[NH2:21][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[Cl:1])[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[N:11]=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 187967424-(4-Chloro-3-nitrobenzyl)amino-6-chloroquinazoline

Product 1

HCID 187967134-(3-Amino-4-chlorobenzyl)amino-6-chloroquinazolineYield 99.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture comprising 1.00 g (2.86 mmol) of 4-(4-chloro-3-nitrobenzyl)amino-6-chloroquinazoline, 0.85 g of powdered iron, 10 ml of acetic acid and 50 ml of ethanol was heated under reflux for several hours and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to give 0.91 g of the title compound as a pale-yellow crystal.

Workup

  1. temperatureunder reflux for several hours
  2. distillationdistilled under a reduced pressure
  3. customto remove the solvent
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-af294240a224421f8155ac07952efc69
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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