Butyl bromide → 5-Butoxypicolinic acid

HRID 2426728Notes

Reaction equation

HRID 2426728 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-db6576de2d6143f88b93f99177f8c873
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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