Sodium Hydroxide → HCID 2748406, compound

HRID 384107Notes

Reaction equation

HRID 384107 reaction equation
[O:1]([C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.B.O1CCCC1.[NH4+]>[O:1]([C:8]1[C:9]([CH2:10][OH:11])=[CH:13][CH:14]=[CH:15][N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 1234503-Pyridinecarboxylic acid, 2-phenoxy-

Product 1

HCID 2748406HCID 2748406, compound

Reagents, catalysts & solvents 3

HCID 223AmmoniumSolventHCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-phenoxynicotinic acid (2.0 g) in tetrahydrofuran (20 ml), 9.5 ml of borane-tetrahydrofuran complex (1.17M tetrahydrofuran solution) was added, and the reaction solution was stirred overnight at 50° C. The reaction solution was cooled, 14 ml of 1N aqueous sodium hydroxide was added under ice-cooling, and the reaction solution was stirred for 1 hour. The reaction solution was diluted with saturated aqueous ammonium solution, extracted with diethyl ether, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-50:50)) to afford the title compound as a colorless oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. temperaturecooling
  3. stirringthe reaction solution was stirred for 1 hour
  4. extractionextracted with diethyl ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-50:50))

Sources & evidence

ORD record
ord-5b117931ceb048a494f75ddf5cee6fdd
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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