Hydrochloric Acid → 1-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 369983Notes

Reaction equation

HRID 369983 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][N:3]=1.[BH4-].[Na+].[ClH:17]>CO>[ClH:17].[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 109322281-Methyl-7-nitro-3,4-dihydroisoquinoline

Product 1

HCID 215843101-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-7-nitro-3,4-dihydroisoquinoline (397 g, 20.9 mmol) in methanol (80 ml) was added sodium borohydride (0.87 g, 23.0 mmol) portionwise. The mixture was stirred for 30 min., acidified with 6N HCl, the solvent was evaporated and the solid was stirred in isopropanol, collected and washed with ether: 5.33 g (>100%); MS (M+H)+ 193.

Workup

  1. customthe solvent was evaporated
  2. stirringthe solid was stirred in isopropanol
  3. customcollected
  4. washwashed with ether

Sources & evidence

ORD record
ord-210841e8a536430f944b649ae733f9ae
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

Loading…