Hydrochloric Acid → HCID 21447055, compound

HRID 597389Notes

Reaction equation

HRID 597389 reaction equation
[N+:1]([C:4]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:5]=1[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:25][CH3:26])=[C:14]([O:17]CC3C=CC=CC=3)[CH:15]=2)[CH2:10][CH2:9][N:8]1[CH3:27])([O-])=O.C(O)C.[ClH:39]>CO.[Pd]>[ClH:39].[ClH:39].[NH2:1][C:4]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:5]=1[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:25][CH3:26])=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH2:9][N:8]1[CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 21447069HCID 21447069, compound

Product 1

HCID 21447055HCID 21447055, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(2'-nitro-4',5'-dimethoxy-benzyl)-2-methyl-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline (1.50 g) in absolute methanol (100 ml) containing palladium-charcoal catalyst (5%, 0.45 g) was stirred under hydrogen until absorption ceased. The catalyst was filtered, washed with methanol and the filtrate evaporated to give an oil. Absolute ethanol (10 ml) was added followed by absolute ethanol saturated with hydrochloric acid gas (10 ml) to give 1-(2'-amino-4',5'-dimethoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (4g) as a white solid (1.18 g, 81%), mp 177°-178°. An analytical sample was evaporated by recrystallization from ethanol, mp 177°-179°.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. customthe filtrate evaporated
  4. customto give an oil

Sources & evidence

ORD record
ord-60096ab18884470db3bee7934e51a34d
Source dataset
uspto-grants-1977_03
Patent number
US04013664

Reaction notes

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