Potassium Carbonate → Methyl 6-hydroxymethyl-3-methylquinoline-2-carboxylate

HRID 1604548Notes

Reaction equation

HRID 1604548 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]([O:18][CH2:19]C)=[O:17])[C:10]([CH3:21])=[CH:9]2)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:10]([CH3:21])=[CH:9]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19603481Ethyl 6-acetoxymethyl-3-methylquinoline-2-carboxylate

Product 1

HCID 19603207Methyl 6-hydroxymethyl-3-methylquinoline-2-carboxylateYield 5.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 6-acetoxymethyl-3-methylquinoline-2-carboxylate (420 mg) and potassium carbonate in methanol was stirred for 30 minutes under ice-cooling. After filtration the filtrate was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with water, dried over magnesium sulfate and concentrated to give methyl 6-hydroxymethyl-3-methylquinoline-2-carboxylate (20 mg).

Workup

  1. temperaturecooling
  2. filtrationAfter filtration the filtrate
  3. concentrationwas concentrated
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88db145c2b284e7a8be0441b53a3e69c
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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