Ethanol → HCID 58980659, compound

HRID 735804Notes

Reaction equation

HRID 735804 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]=C(C#N)[C:6]=1[O:17][CH3:18])C.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>>[C:11]([C:9]1[N:8]=[C:23]([C:22]([OH:20])=[O:24])[C:6]([O:17][CH3:18])=[C:5]([C:4]([OH:3])=[O:19])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68892076HCID 68892076, compound

Product 1

HCID 58980659HCID 58980659, compoundYield 68%

Procedure

To a solution of the above nitrile (616 mg, 2.35 mmol) in ethanol (8.0 mL) was added NaOH (2.0 M in water, 8.3 mL, 16.5 mmol). The mixture was heated to reflux for 20 h then cooled to room temperature and the ethanol was concentrated in vacuo. The basic solution was neutralized with 12 N HCl to a pH=6 then extracted with chloroform/isopropanol (3:1). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 6-tert-butyl-3-methoxy-pyridine-2,4-dicarboxylic acid (402 mg, 68%) as a yellow solid which was utilized without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 20 h
  3. concentrationthe ethanol was concentrated in vacuo
  4. extractionthen extracted with chloroform/isopropanol (3:1)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e57656e2061d4eba99b42812c222a8a2
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

Loading…