Ammonia → HCID 66772617, compound

HRID 1644555Notes

Reaction equation

HRID 1644555 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.[NH3:23]>C(OCC)(=O)C>[NH2:23][C:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[CH:5]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 667722916-Chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline

Product 1

HCID 66772617HCID 66772617, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.45 g of 6-chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline and 30 ml of ammonia-saturated THF solution was heated in an autoclave at 80° C. for 10 hours and then at 12° C. for a further 15 hours. Subsequent MPLC on an MPRC cartridge and a mixture of 20 parts by volume of ethyl acetate:10 parts by volume of n-heptane:3 parts by volume of glacial acetic acid leads to elution of starting material (6-chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline). Subsequent elution with methanol results in 1-amino-6-chloro-4-(4-nitrophenyl)-3,4-dihydroisoquinoline.

Workup

  1. wash10 parts by volume of n-heptane:3 parts by volume of glacial acetic acid leads to elution of starting material (6-chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline)
  2. washSubsequent elution with methanol
  3. customresults in 1-amino-6-chloro-4-(4-nitrophenyl)-3,4-dihydroisoquinoline

Sources & evidence

ORD record
ord-1eb08dad910146d6b46c58985a8a509b
Source dataset
uspto-grants-2012_02
Patent number
US08124621B2

Reaction notes

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