Hydrochloric Acid → HCID 13560532, compound

HRID 638072Notes

Reaction equation

HRID 638072 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[N:8][CH2:7]1)=[O:5].C1C2C(CCCC2)CCC1.Cl>[Pd].O>[CH3:2][O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[N:8][CH:7]=1)=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7044DecalinHCID 131714344HCID 131714344, compound

Product 1

HCID 13560532HCID 13560532, compoundYield 115.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 3.9 g of 3,4-dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinoline carboxylic acid methyl ester, hydrochloride, 100 ml of decalin and 2 g of 10% palladium on carbon was stirred and refluxed for 2 hours. The cooled mixture was diluted with water, acidified with 6N hydrochloric acid, and the catalyst was removed by filtration. The aqueous solution was washed with ether, made basic with excess ammonium hydroxide, and the product was extracted with ethyl acetate, dried, and evaporated to give 4.1 g of crude 6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinolinecarboxylic acid methyl ester. Crystallization from ether provided the analytically pure material, mp 127°-128°.

Workup

  1. temperaturerefluxed for 2 hours
  2. customthe catalyst was removed by filtration
  3. washThe aqueous solution was washed with ether
  4. extractionthe product was extracted with ethyl acetate
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-8ccd428f22274e3ab98736643f60fa59
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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