HCID 90411669, compound → HCID 83873140, compound

HRID 717389Notes

Reaction equation

HRID 717389 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[CH:9][C:8]([CH3:12])=[C:7]([OH:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[H][H]>[Pd]>[OH:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[CH2:5][CH2:4][NH:3][CH2:2]2

Participants

4

Reactant 2

HCID 90411669HCID 90411669, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 83873140HCID 83873140, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethanol (20 mL). To the above hydrogen chloride (enough, gas) was introduced in. This was followed by the addition of 1-chloro-6-methylisoquinolin-5-ol (70 mg, 0.36 mmol, 1.00 equiv), Pd/C (30 mg). To the above hydrogen (enough, gas) was introduced in. The resulting solution was stirred overnight at room temperature with an inert atmosphere of H2 (gas). The resulting mixture was concentrated under vacuum. The resulting mixture was washed with 1×10 mL of ether. This resulted in 50 mg (69%) of 5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride as an off-white solid. 1H NMR (300 MHz, D2O) δ 2.72 and 2.16 (s, 3H), 2.93 (t, 2H), 3.45 (t, 2H), 4.25 (s, 2H), 6.69 (d, 1H), 7.06 (d, 1H); MS (ESI) m/z 164 ([M+H]+).

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionTo the above hydrogen chloride (enough, gas) was introduced in
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. washThe resulting mixture was washed with 1×10 mL of ether
  6. customThis resulted in 50 mg (69%) of 5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride as an off-white solid

Sources & evidence

ORD record
ord-1dcd06e123f2495ead4ba577c0276400
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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