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

HRID 229039Notes

Reaction equation

HRID 229039 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, and the reaction solution was then washed with diethyl ether and was neutralized with potassium carbonate powder. Diethyl ether was added thereto, the mixture was extracted, and 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-0b7ed7124e894fc2902e286c1935bbe7
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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