Potassium Carbonate → 6-(Quinol-2-ylmethoxy)nicotinic acid methyl ester

HRID 1721687Notes

Reaction equation

HRID 1721687 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[N:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178498304HCID 178498304, compound

Product 1

HCID 539871676-(Quinol-2-ylmethoxy)nicotinic acid methyl esterYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxynicotinic acid methyl ester (10.0g, 0.0652 mol), prepared as in step 1, in DMF (350 ml) at room temperature was added anhydrous K2CO3 (19.0 g, 0.137 mol) followed by 2-chloromethylquinoline hydrochloride (14.0 g, 0.0652 mol), and the mixture was allowed to stir at room temperature overnight. Once the starting material was consumed, water (700 ml) was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting white precipitate was filtered and washed with hexanes to give 15.20 g of 6-(quinol-2-ylmethoxy)nicotinic acid methyl ester.

Workup

  1. customOnce the starting material was consumed
  2. additionwater (700 ml) was added to the mixture
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. filtrationThe resulting white precipitate was filtered
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-f94de0205dbc44b29b501f0362f4c8ba
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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