HCID 12464194, compound → HCID 18180253, compound

HRID 1106576Notes

Reaction equation

HRID 1106576 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2>Cl.O.[Pt](=O)=O>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1

Participants

5

Reactant 1

HCID 12464194HCID 12464194, compound

Product 1

HCID 18180253HCID 18180253, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 3-methoxyisoquinoline (800 mg, 5.03 mmol) and platinum dioxide (100 mg) in concentrated hydrochloric acid (10 ml) was shaken under an atmosphere of hydrogen at 40 psi for 5 h. The mixture was diluted with water, filtered through Celite™, basified with sodium hydroxide then extracted four times with ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated to afford the title compound (600 mg) as a clear oil, MS (ES+) 164 (MH+). δH (CDCl3) 7.85 (1H, s), 6.43 (1H, s), 3.87 (3H, s), 2.65 (4H, m) and 1.75 (4H, m).

Workup

  1. filtrationfiltered through Celite™
  2. extractionthen extracted four times with ethyl acetate
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b07147206794d979d1900358d1a5a64
Source dataset
uspto-grants-2000_05
Patent number
US06057329

Reaction notes

Loading…