Potassium Hydroxide → HCID 67205909, compound

HRID 1894323Notes

Reaction equation

HRID 1894323 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#N)=[C:7]([O:13][CH2:14][CH3:15])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:16].[K+].C(O)C.[OH2:21]>>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]([OH:21])=[O:16])=[C:7]([O:13][CH2:14][CH3:15])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 67205406HCID 67205406, compound

Product 1

HCID 67205909HCID 67205909, compoundYield 95%

Conditions

Temperature
90 °C

Procedure

6-tert-Butyl-2-ethoxy-nicotinonitrile (1.10 g, 5.3 mmol, prepared according to the literature procedure by Youngdale, G. A. and T. F. Oglia J. Med. Chem. 1985, 28, 1791) and potassium hydroxide (1.80 g, 32.3 mmol) were combined in ethanol/water (30 ml/7 ml) and heated at 90° C. overnight. The reaction was concentrated, acidified with 2N hydrochloric acid solution (20 ml) and extracted with chloroform. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated to give 6-tert-butyl-2-ethoxy-nicotinic acid as a white solid (1.00 g, 95%) LR-MS: 222 [(M−H)+]

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with chloroform
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f199ecfdfe31418eb4d2fe6f7ecb3ea6
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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