Butyl bromide → 5-Butoxypicolinic acid

HRID 1354781Notes

Reaction equation

HRID 1354781 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:11])=[N:8][CH:9]=1.Br[CH2:27][CH2:28][CH2:29][CH3:30]>CN(C=O)C.O>[CH2:27]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 21105536HCID 21105536, compound

Product 1

HCID 1738725-Butoxypicolinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydride (50% in oil, 250 mg) was added to benzhydryl 5-hydroxypyridine-2-carboxylate (2.0 g) dissolved in DMF (20 ml) and, after gas evolution ceased, 1-bromobutane (0.72 g) was added. The mixture was heated at 90° C. for 6 hours. It was diluted with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was hydrogenated in analogy to method B. This resulted in the product with the molecular weight of 195.22 (C10H13NO3); MS (ESI): 196 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThis resulted in the product with the molecular weight of 195.22 (C10H13NO3)

Sources & evidence

ORD record
ord-b4150b5f284745b2acab0d9a2c6a3e00
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

Loading…