Hydrochloric Acid → HCID 67823539, compound

HRID 1108903Notes

Reaction equation

HRID 1108903 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 CH2 /Cl2 /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 CH2 /Cl2 /i-PrOH

Sources & evidence

ORD record
ord-c9845a52b1b94e7caed490482d665033
Source dataset
uspto-grants-1994_06
Patent number
USRE034630

Reaction notes

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