Methanol → HCID 21393876, compound

HRID 1288479Notes

Reaction equation

HRID 1288479 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([Cl:15])[C:8]([Cl:14])=[CH:9][CH:10]=2)[CH2:5]1)(=O)[CH3:2].B#B.CO>O1CCCC1>[ClH:14].[Cl:14][C:8]1[C:7]([Cl:15])=[C:6]2[C:11]([CH2:12][CH2:13][N:4]([CH2:1][CH3:2])[CH2:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6328200DiboronHCID 125951001-(7,8-Dichloro-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

Product 1

HCID 21393876HCID 21393876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Acetyl-7,8-dichloro-1,2,3,4-tetrahydroisoquinoline is treated with excess diborane in tetrahydrofuran and refluxed for 16 hours. Methanol is added to destroy excess diborane and the solvent is removed in vacuo. The residue is dissolved in ether, treated with hydrogen chloride and filtered to give 7,8-dichloro-2-ethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride.

Workup

  1. temperaturerefluxed for 16 hours
  2. customto destroy excess diborane
  3. customthe solvent is removed in vacuo
  4. dissolutionThe residue is dissolved in ether
  5. additiontreated with hydrogen chloride
  6. filtrationfiltered

Sources & evidence

ORD record
ord-63308174426e4e1cbcb81f9b6801a2e7
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

Loading…