HCID 21447050, compound → HCID 21447048, compound

HRID 597387Notes

Reaction equation

HRID 597387 reaction equation
[N+:1]([C:4]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([Br:27])=[CH:21][C:5]=1[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH2:9][N:8]1[CH3:20])([O-])=O>CO.[Pd]>[BrH:27].[NH2:1][C:4]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:5]=1[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH2:9][N:8]1[CH3:20]

Participants

4

Reactant 1

HCID 21447050HCID 21447050, compound

Product 1

HCID 21447048HCID 21447048, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(2'-nitro-4'-methoxy-5'-bromobenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (3c) (850 mg) in absolute methanol (80 ml) containing palladium-charcoal catalyst (5%, 250 mg) was stirred under hydrogen until absorption ceased (approximately 6-8 hours). The catalyst was filtered, washed with methanol and the filtrate evaporated to give an oil which was crystallized from acetone to give white crystals of 1-(2'-amino-4'-methoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (4f) (735 mg, 81%), mp 136°-137.5°. An analytical sample was prepared by recrystallization from acetone, mp 137.5°-138°; nmr δ (CDCl3), 2.05 (s, 6H, acetone CH3COCH3), 2.78 (s, 3H, NCH3), 3.88 and 3.92 (2s, 6H, 2OCH3), and 5.94-6.57 (CM, 5H, aromatic H).

Workup

  1. custom(approximately 6-8 hours)
  2. filtrationThe catalyst was filtered
  3. washwashed with methanol
  4. customthe filtrate evaporated
  5. customto give an oil which
  6. customwas crystallized from acetone

Sources & evidence

ORD record
ord-b5c2abfe14fd47d494bd997f0b0e4518
Source dataset
uspto-grants-1977_03
Patent number
US04013664

Reaction notes

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