Tetralin → HCID 15068905, compound

HRID 1031904Notes

Reaction equation

HRID 1031904 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-1e61b5711dac4994a88862ec03911862
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Reaction notes

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