Potassium Carbonate → 3,4-Dihydro-5-hydroxy-6-methoxy-1(2H)-isoquinolinone

HRID 717365Notes

Reaction equation

HRID 717365 reaction equation
C(=O)([O:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][C:11]2=[O:18])OCC.C([O-])([O-])=O.[K+].[K+]>CO>[OH:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][C:11]2=[O:18]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 90410952Ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl carbonate

Product 1

HCID 904103403,4-Dihydro-5-hydroxy-6-methoxy-1(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 50-mL 3-necked round-bottom flask, was placed ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl carbonate (1.5 g, 5.65 mmol, 1.00 equiv), methanol (20 mL) and K2CO3 (2.34 g, 16.81 mmol, 3.00 equiv). The resulting solution was stirred for 3 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate (100%). This resulted in 0.7 g (64%) of 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-one as a off-white solid. 1H NMR (300 MHz, DMSO-d6) δ: 2.83 (m, 2H), 3.78 (s, 3H), 4.14 (s, 2H), 6.63-6.66 (2s, 1H), 6.88-6.91 (2s, 1H); MS (ESI) m/z 194 ([M+H]+).

Workup

  1. customInto a 50-mL 3-necked round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 0.7 g (64%) of 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-one as a off-white solid

Sources & evidence

ORD record
ord-6bf512e3b85644dc90148efbef1fe828
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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