HCID 12707063, compound → HCID 12707067, compound

HRID 973041Notes

Reaction equation

HRID 973041 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.[H][H]>C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[C:14]2[CH2:27][C:28]1[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=1

Participants

5

Reactant 2

HCID 12707063HCID 12707063, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12707067HCID 12707067, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.2 g of 5.7-dibenzyloxy-1-(3,4,5-trimethoxybenzyl)-isoquinoline is dissolved in 250 ml of ethanol, and 0.05 g ot 10% palladium-carbon is added thereto. The mixture is shaken at 25° C in a hydrogen atmosphere. After the hydrogen uptake is completed, the catalyst is removed by filtration. The filtrate is evaporated to remove solvent. 0.125 g of 5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-isoquinoline is thereby obtained as a crude product. Yield: 95% M.p. 270° - 275° C (decomp.) (recrystallized from ethanol).

Workup

  1. customthe catalyst is removed by filtration
  2. customThe filtrate is evaporated
  3. customto remove solvent

Sources & evidence

ORD record
ord-d85b2012aa5d46d0be20f185f93f8aad
Source dataset
uspto-grants-1977_10
Patent number
US04054659

Reaction notes

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