Butyl bromide → 5-Butoxypicolinic acid

HRID 2043101Notes

Reaction equation

HRID 2043101 reaction equation
[H-].[Na+].C([O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][N:20]=1)=[O:18])(C1C=CC=CC=1)C1C=CC=CC=1.Br[CH2:27][CH2:28][CH2:29][CH3:30]>CN(C=O)C.O>[CH2:27]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]([OH:16])=[O:18])=[N:20][CH:21]=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 5-hydroxypyridine-2-carboxylic acid benzhydryl ester (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. The product with the molecular weight of 195.22 (C10H13NO3); MS (ESI): 196 (M+H+) was obtained in this way.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customMS (ESI): 196 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-d9beccc222114cd6a594642d3e71b313
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

Loading…