Benzyl Alcohol → 2-(Benzyloxy)pyridine-4-carboxylic acid

HRID 852065Notes

Reaction equation

HRID 852065 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][N:20]=1)[C:15]([OH:17])=[O:16].Cl>CN(C)C=O.O>[CH2:3]([O:10][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][N:20]=1)[C:15]([OH:17])=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 229262722-(Benzyloxy)pyridine-4-carboxylic acidYield 34.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (14.0 g) in N,N-dimethylformamide (250 mL) was added dropwise benzyl alcohol (20.6 g) under ice-cooling over 30 minutes and then added 2-chloroisonicotinic acid (25.0 g) thereto. The reaction solution was stirred at room temperature for 2 hours and then at 70° C. for 13 hours. The reaction solution was allowed to cool to room temperature, diluted with about decuple volumes of water, and then adjusted to pH 5 with 5N hydrochloric acid. The resulting crystals were collected by filtration and then washed with water and hexane to give the title compound as a colorless solid (12.6 g).

Workup

  1. temperaturecooling over 30 minutes
  2. waitat 70° C. for 13 hours
  3. temperatureto cool to room temperature
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water and hexane

Sources & evidence

ORD record
ord-e19f5781b57d482ba8ee4a922d130500
Source dataset
uspto-grants-2007_08
Patent number
US07253178B2

Reaction notes

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