HCID 21447071, compound → HCID 21447044, compound

HRID 597385Notes

Reaction equation

HRID 597385 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[C:4]=1[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[CH2:9][CH2:8][N:7]1[CH3:19].[H][H]>C(O)C.[Pd]>[NH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[CH2:9][CH2:8][N:7]1[CH3:19]

Participants

5

Reactant 2

HCID 21447071HCID 21447071, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21447044HCID 21447044, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the 1-(2'-methoxy-6'-nitrobenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (3b) (1 g) and 5% palladium-charcoal (0.2 g) in absolute ethanol (150 ml) was shaken with hydrogen at room temperature and atmospheric pressure overnight (19 hours). The mixture was filtered through celite, and the filtrate was evaporated to dryness to leave a transparent brown oil. This crystallized from methanol-ether to give 1-(2'-amino-6'-methoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (4b) (0.885 g, 93%), mp 158°-160°. Recrystallization from absolute ethanol gave feathery needles, mp 161°-162°; λmaxKBr 2.88 and 2.96 μ (OH and NH2); λmaxEtOH (c) 285.5 nm (5480); nmr τ 3.02-3.87 (5H, aromatic H), 6.24 (6H, s, O--CH3), and 7.66 (3H, s, N--CH3); mass spectrum m/e 327 (M+ - 1), 296, 205, 192, 177, and 148.

Workup

  1. customatmospheric pressure overnight (19 hours)
  2. filtrationThe mixture was filtered through celite
  3. customthe filtrate was evaporated to dryness
  4. customto leave a transparent brown oil
  5. customThis crystallized from methanol-ether

Sources & evidence

ORD record
ord-0f9c5a3f1cd94bb48f623016f38dc8d8
Source dataset
uspto-grants-1977_03
Patent number
US04013664

Reaction notes

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