Hydrochloric Acid → HCID 21403372, compound

HRID 973043Notes

Reaction equation

HRID 973043 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]([O:19]CC2C=CC=CC=2)[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[C:14]2[CH2:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)C1C=CC=CC=1.[ClH:40].C(O)C.Cl.C(O)C>[H][H].[Pt](=O)=O>[ClH:40].[OH:8][C:9]1[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][CH:14]2[CH2:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12707063HCID 12707063, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 21403372HCID 21403372, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1.4 g of 5,7-dibenzyloxy-1-(3,4,5-trimethoxybenzyl)-isoquinoline, 0.7 g of platinum dioxide, 100 ml of a hydrochloric acid-ethanol solution (the content of hydrochloric acid: 9%) and 50 ml of ethanol is shaken at 25° C in hydrogen atmosphere. After 150 ml of hydrogen are absorbed, the catalyst is removed by filtration. The filtrate is evaporated to remove solvent, whereby a mixture of 5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-isoquinoline hydrochloride and 5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride is obtained. This mixture is recrystallized 33 times from ethanol, whereby 0.3 g of 5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydrolsoquinoline hydrochloride is obtained. Yield: 40% The physiocochemical properties of this product are identical with those of the compound obtained in Example 1.

Workup

  1. customAfter 150 ml of hydrogen are absorbed
  2. customthe catalyst is removed by filtration
  3. customThe filtrate is evaporated
  4. customto remove solvent, whereby
  5. additiona mixture of 5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-isoquinoline hydrochloride

Sources & evidence

ORD record
ord-15114816061a4ba4858e5eac3ab30735
Source dataset
uspto-grants-1977_10
Patent number
US04054659

Reaction notes

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