Tetralin → HCID 15068905, compound

HRID 1108906Notes

Reaction equation

HRID 1108906 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C2C(=CC=CC=2)CCC1>CCOCC.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 8404TetralinHCID 15068904HCID 15068904, compound

Product 1

HCID 15068905HCID 15068905, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(3,4-dimethoxyphenyl)-6-methyl-3, 4-dihydroisoquinoline (C2) (5.0 g, 0.018 mol), 10% Pd/C (400 mg) and tetralin (50 ml) was boiled under nitrogen for 3.75 h. The cooled reaction mixture was diluted with ether and filtered The filtrate was treated with HCl gas to give 5.4 g (98%) of the title compound as the hydrochloride. A sample was recrystallized from i-PrOH to give pure 1-(3,4-dimethoxyphenyl)-6-methylisoquinoline hydrochloride, mp 225° dec.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered The filtrate
  3. additionwas treated with HCl gas

Sources & evidence

ORD record
ord-9b0cbf50760140069cebabac2f69b6b6
Source dataset
uspto-grants-1994_06
Patent number
USRE034630

Reaction notes

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