Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate → Methyl 6-hydroxyisoquinoline-3-carboxylate

HRID 1640121Notes

Reaction equation

HRID 1640121 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5]2>[Pd].CO>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2

Participants

4

Reactant 1

HCID 10420549Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Product 1

HCID 135742191Methyl 6-hydroxyisoquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (0.72 g, 3.5 mmol) in xylenes (70 mL) was added 10% palladium on carbon (0.58 g). The mixture was heated at reflux for 18 h, and then cooled to rt. MeOH (5 mL) was added and the mixture was filtered through Celite. The solvents were evaporated and the residue was purified by column chromatography give methyl 6-hydroxyisoquinoline-3-carboxylate as yellow solid. (0.26 g, 36%). LCMS: (FA) ES+ 204.0, ES− 202.0.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. filtrationthe mixture was filtered through Celite
  4. customThe solvents were evaporated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9b63aa444aed41ff97dc3a882f6a8347
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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