HCID 21403370, compound → HCID 21403372, compound

HRID 973042Notes

Reaction equation

[ClH:1].C([O:5][C:6]1[CH:15]=[C:14]([O:16]C(=O)C)[CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[C:11]2[CH2:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1)(=O)C.[H][H]>C(O)C.[Pt](=O)=O>[ClH:1].[OH:5][C:6]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][CH:11]2[CH2:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

0.78 g of 5,7-diacetoxy-1-(3,4,5-trimethoxybenzyl)-isoquinoline hydrochloride is dissolved in 200 ml of ethanol, and 0.3 g of platinum dioxide 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. 50 ml of a hydrochloric acid-ethanol solution (the content of hydrochloric acid: 9%) are added to the filtrate, and this mixture is heated at 50° C for 5 minutes. Then, the mixture is evaporated to remove solvent, and the residue thus obtained is recrystallized from a mixture of ethanol and isopropyl ether. 0.6 g of 5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride is thereby obtained. Yield: 94.6% M.p. 240° - 243° C.

Workup

customthe catalyst is removed by filtration
addition50 ml of a hydrochloric acid-ethanol solution (the content of hydrochloric acid: 9%) are added to the filtrate
customThen, the mixture is evaporated
customto remove solvent
customthe residue thus obtained
customis recrystallized from a mixture of ethanol and isopropyl ether

Sources & evidence

ORD record: ord-32cd874f27c54c48a5cefb07509c099a
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04054659

Reaction notes

Loading…