N-(3-formylpyridin-4-yl)-2,2-dimethylpropanamide → 4-Aminonicotinaldehyde

HRID 228903

Reaction equation

HRID 228903 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[NH:9]C(=O)C(C)(C)C)=[O:2]>Cl>[NH2:9][C:8]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:1]=[O:2]

Participants

3

Procedure

N-(3-Formyl-pyridin-4-yl)-2,2-dimethyl-propionamide (3.35 g) was dissolved in 3 N hydrochloric acid (50 ml) to prepare a solution which was stirred under reflux for 5.5 hr. The reaction solution was cooled to room temperature, the reaction solution was then washed with diethyl ether and was neutralized with potassium carbonate powder. Diethyl ether was added thereto, and the mixture was extracted. The diethyl ether layer was dried over potassium carbonate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 4-amino-pyridine-3-carbaldehyde (1.12 g, yield 58%).

Workup

  1. customto prepare a solution which
  2. temperatureunder reflux for 5.5 hr
  3. washthe reaction solution was then washed with diethyl ether
  4. additionDiethyl ether was added
  5. extractionthe mixture was extracted
  6. dry with materialThe diethyl ether layer was dried over potassium carbonate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8ab4d20ef8f94c6cb1798d6d98796040
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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