4-Methyloxybenzyl chloride → HCID 47143064, compound

HRID 1790802Notes

Reaction equation

HRID 1790802 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:7][C:6]([C:5]2[CH:9]=[CH:10][C:2](=[O:1])[NH:3][CH:4]=2)=[O:8])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxideHCID 178418479HCID 178418479, compound

Product 1

HCID 47143064HCID 47143064, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-hydroxynicotinic acid (4.87 g, 35 mmol) in DMF (100 mL) at room temperature, was added potassium tert-butoxide (3.93 g, 35 mmol). The reaction mixture was stirred at 60° C. for 1 h. 4-Methoxybenzylchloride (8.30 g, 53 mmol) was added and the reaction mixture was stirred at 60° C. for 4 h. The DMF was evaporated under vacuum, the residue was dissolved in ether (200 mL) and washed with water (3×100 mL). The organic phase was dried with Na2SO4 and evaporated to give 4.41 g of 6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester.

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 4 h
  2. customThe DMF was evaporated under vacuum
  3. dissolutionthe residue was dissolved in ether (200 mL)
  4. washwashed with water (3×100 mL)
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-f1bfc1bbd53e4502bb8a5a2ecf296c94
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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