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

HRID 480567Notes

Reaction equation

HRID 480567 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-934d6f78299e494b95a70a5c272746ec
Source dataset
uspto-grants-2003_11
Patent number
US06653302B2

Reaction notes

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