Methylamine → 6-chloro-N-methyl-4-(4-nitrophenyl)-3,4-dihydroisoquinolin-1-amine

HRID 1644557Notes

Reaction equation

HRID 1644557 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](SC)=[N:7][CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.[CH3:23][NH2:24]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:24][CH3:23])=[N:7][CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 667722916-Chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline2×

Product 1

HCID 1784823576-chloro-N-methyl-4-(4-nitrophenyl)-3,4-dihydroisoquinolin-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

400 mg of 6-chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline (see compound 1e) were heated with 2 g of methylamine in THF at 120° C. in a shaking autoclave under inert gas for 20 hours. Removal of the solvent by distillation was followed by MPLC chromatography on an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation
  3. additionwas followed by MPLC chromatography on an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution

Sources & evidence

ORD record
ord-086180549cc3443d8396f1b5085ecbe2
Source dataset
uspto-grants-2012_02
Patent number
US08124621B2

Reaction notes

Loading…