Hydrochloric Acid → 2-[(Propan-2-yl)oxy]pyridine-4-carboxylic acid

HRID 1983581Notes

Reaction equation

HRID 1983581 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][N:12]=1)[C:8]#N)([CH3:3])[CH3:2].[OH-:13].[Na+].Cl.[OH2:16]>C(O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][N:12]=1)[C:8]([OH:16])=[O:13])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 24692243HCID 24692243, compound

Product 1

HCID 177509332-[(Propan-2-yl)oxy]pyridine-4-carboxylic acidYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of step 1 (1.25 g, 7.71 mmol) in ethanol (20 mL) was treated with 10 N aqueous sodium hydroxide solution (10 mL) and heated to reflux. After 1 hour, the mixture was cooled to room temperature and diluted with water. Concentrated hydrochloric acid was added to attain pH=4, and the resulting precipitate was isolated by filtration. The material was washed with water and dried in vacuo to provide 0.920 g (66%) of product as a white solid: 1H NMR (CDCl3) δ 12.1 (br s, 1H), 8.32 (d, J=5.2 Hz, 1H), 7.42 (dd, J=5.2, 1.4 Hz, 1H), 7.33 (d, J=1.4 Hz, 1H), 5.32 (sept, J=6.1 Hz, 1H), 1.37 (d, J=6.1 Hz, 6H) ppm. 13C NMR (CDCl3) δ 170.0, 164.2, 147.9, 139.2, 115.4, 112.5, 68.9, 21.9 ppm.

Workup

  1. temperatureheated to reflux
  2. customthe resulting precipitate was isolated by filtration
  3. washThe material was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a82e9707979b4abfa297a832e31f4f65
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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