Sulfuric Acid → 8-Amino-5-(4-chlorophenyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloric acid salt

HRID 736439Notes

Reaction equation

HRID 736439 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]3[C:9]=2[CH2:10][CH2:11][N:12]([CH3:21])[CH2:13]3)=[CH:4][CH:3]=1.S(=O)(=O)(O)O>[Ni].CO>[ClH:1].[NH2:18][C:15]1[CH:16]=[CH:17][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:9]2[C:14]=1[CH2:13][N:12]([CH3:21])[CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 234358215-(4-Chlorophenyl)-N-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 234358398-Amino-5-(4-chlorophenyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloric acid salt

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(4-Chlorophenyl)-N-methyl-8-nitro-1,2,3,4-tetrahydroiso-quinoline (3.47 g, 11.5 mmol), sulphuric acid (1 ml, 12 mmol), Raney nickel (1 ml, 50% slurry in water) and methanol (150 ml) was stirred under hydrogen for 1.5 h. The crude mixture was filtered through celite and was evaporated. Yield 3.2 g (90%). Mp 213-215° C.

Workup

  1. filtrationThe crude mixture was filtered through celite
  2. customwas evaporated

Sources & evidence

ORD record
ord-c06d7fe4f7ac4ac0b88158777e3a5b8c
Source dataset
uspto-grants-2009_09
Patent number
US07595336B2

Reaction notes

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