Ammonia → N*4*-(3,4-Dichlorobenzyl)-2-methylquinoline-4,8-diamine

HRID 1966511Notes

Reaction equation

HRID 1966511 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1.[NH3:23]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[Cl:21])[CH2:14][NH:13][C:7]1[C:6]2[C:11](=[C:2]([NH2:23])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([CH3:12])[CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59474780(8-Bromo-2-methylquinolin-4-yl)-(3,4-dichlorobenzyl)-amine

Product 1

HCID 59474762N*4*-(3,4-Dichlorobenzyl)-2-methylquinoline-4,8-diamineYield 52%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent

Procedure

(8-Bromo-2-methylquinolin-4-yl)-(3,4-dichlorobenzyl)-amine (500 mg, 1.26 mmole), copper(II)sulphate pentahydrate (316 mg, 1.27 mmole) and ammonia (20% in water/ethanol 1:1, 20 mL) were stirred in a microwave oven at 150° C. for 5 hrs. The reaction mixture was dissolved in water and extracted with dichloromethane. The resulting organic phases were dried and purified using silica gel chromatography, eluting with dichloromethane:water 99:1. Precipitation in isopropyl ether gave a brownish solid (220 mg, 52%).

Workup

  1. extractionextracted with dichloromethane
  2. customThe resulting organic phases were dried
  3. custompurified
  4. washeluting with dichloromethane:water 99:1
  5. customPrecipitation in isopropyl ether

Sources & evidence

ORD record
ord-c4e1c1cac3304d5494ab76c63d216eb2
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

Loading…