Hydrochloric Acid → 6-(4-Methoxybenzyloxy)nicotinic acid

HRID 2238832Notes

Reaction equation

HRID 2238832 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=1.Cl>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 792226-Chloronicotinic acid

Product 1

HCID 231441716-(4-Methoxybenzyloxy)nicotinic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Methoxybenzyl alcohol (11.9 mL, 95.2 mmol) was dissolved in DMF (150 mL), and at 0° C., 55% sodium hydride (4.15 g, 95.2 mmol) was added thereto, followed by stirring at room temperature for 1 hour. A DMF (10 mL) solution of 6-chloronicotinic acid (5.00 g, 31.7 mmol) was added to the reaction mixture, followed by stirring at 80° C. for 2 hours. Water (200 mL) was added to the reaction mixture, and 4 mol/L hydrochloric acid (30 mL) was added dropwise thereto, and the precipitated solid was collected by filtration to afford 6-(4-methoxybenzyloxy)nicotinic acid (8.15 g, 99%).

Workup

  1. stirringby stirring at 80° C. for 2 hours
  2. additionwas added dropwise
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-cadbd6104468408393a0cd6dffd326c6
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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