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

HRID 2307769Notes

Reaction equation

HRID 2307769 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[C:3]([CH:1]=[O:2])=[CH:4][N:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 2779664N-(3-formylpyridin-4-yl)-2,2-dimethylpropanamide

Product 1

HCID 27610334-AminonicotinaldehydeYield 87.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of Example 25B (870 mg, 4.2 mmol) in 3N HCl (aq.) (10 mL) was heated to reflux overnight, and extracted three times with diethyl ether. The aqueous layer was adjusted to pH >7 with solid K2CO3 and extracted six times with 20% isopropanol/chloroform. The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product (450 mg; 87%).

Workup

  1. temperatureto reflux overnight
  2. extractionextracted three times with diethyl ether
  3. extractionextracted six times with 20% isopropanol/chloroform
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ff5100f24b2405ba53b71da65ac26b8
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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