Hydrochloric Acid → 5-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 840146

Reaction equation

HRID 840146 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.Cl>CCO.[Pt]=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 137542835-Methoxyisoquinoline

Product 1

HCID 139482495-Methoxy-1,2,3,4-tetrahydroisoquinolineYield 95%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of step (a) (6.11 g, 384 mmol) in EtOH (200 ml) was added platinum oxide (0.611 g) followed by concentrated HCl (3.2 ml, 38.4 mmol). The reaction mixture was hydrogenated at 345 kPa (50 p.s.i.) at room temperature for 4 h after which time the catalyst was filtered off and washed with EtOH. The filtrate was evaporated under reduced pressure to afford the subtitle compound as a colourless solid (7.27 g, 95%). 1H NMR (D6-DMSO) δ: 2.80 (2H, m), 3.35 (2H, m), 3.80 (3H, s), 4.20 (2H, s), 6.80 (1H, d), 6.90 (1H, d), 7.20 (1H, t), 9.45 (2H, bs).

Workup

  1. filtrationafter which time the catalyst was filtered off
  2. washwashed with EtOH
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4898dd8c83dc4db880dad110fb6ed90e
Source dataset
uspto-grants-2002_04
Patent number
US06365599B1

Linked notes

Loading…