Hydrochloric Acid → HCID 67823539, compound

HRID 1031901Notes

Reaction equation

HRID 1031901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[ClH:21]>C1C2C(=CC=CC=2)CCC1.CCOCC.[Pd]>[ClH:21].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15068901HCID 15068901, compound

Product 1

HCID 67823539HCID 67823539, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8404TetralinSolvent

Procedure

A sample of 1-(3,4-dimethoxyphenyl) 3,4-dihydroisoquinoline (A2) from 3.0 g of the hydrochloride (9.9 mmol) was boiled with 10% Pd/C (240 mg) in tetralin (30 ml). After 3 h the reaction was complete by tlc and the cooled mixture was diluted with ether and the catalyst was filtered. The filtrate was treated with HCl gas and the precipitated hydrochloride was collected by filtration. Recrystallization from CH2Cl2 /i-PrOH afforded 700 mg (23%) of pure 1-(3,4-dimethoxyphenyl) isoquinoline hydrochloride, mp 208-228° dec.

Workup

  1. filtrationthe catalyst was filtered
  2. additionThe filtrate was treated with HCl gas
  3. filtrationthe precipitated hydrochloride was collected by filtration
  4. customRecrystallization from CH2Cl2 /i-PrOH

Sources & evidence

ORD record
ord-95ee9f64ebcf46179e5b09a2361e7ca2
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Reaction notes

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