Sodium Carbonate → 3-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

HRID 2205407

Reaction equation

HRID 2205407 reaction equation
C(O[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=2)[C:9]([OH:23])=[C:8]([C:24]([O:26][CH3:27])=[O:25])[N:7]=1)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C(OCC)(=O)C>[OH:23][C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[C:6]([CH3:5])=[N:7][C:8]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 86709145Methyl 1-(acetoxymethyl)-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A reactor was charged with 1c (16.0 g), Pd/C (2.08 g), anhydrous Na2CO3 (2.56 g) and ethyl acetate (120 mL). The flask was vacuum-purged with nitrogen (3×) and vacuum-purged with hydrogen (3×). The flask was then pressurized with hydrogen and stirred at about 60° C. until completion of reaction. The flask was cooled to 20-25° C., the pressure released to ambient, the head space purged with nitrogen three times and mixture was filtered. The filtrate was concentrated. Methanol was added. The mixture was stirred and then cooled. Product precipitated and was filtered and dried in an oven (Yield: 90%, HPLC: 99.7%).

Workup

  1. customThe flask was vacuum-purged with nitrogen (3×)
  2. customvacuum-purged with hydrogen (3×)
  3. temperatureThe flask was cooled to 20-25° C.
  4. customthe head space purged with nitrogen three times and mixture
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated
  7. additionMethanol was added
  8. stirringThe mixture was stirred
  9. temperaturecooled
  10. customProduct precipitated
  11. filtrationwas filtered
  12. customdried in an oven (Yield: 90%, HPLC: 99.7%)

Sources & evidence

ORD record
ord-3aedda5361b745d1ba41db2f3a78a310
Source dataset
uspto-grants-2016_06
Patent number
US09371288B2

Linked notes

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