Potassium Carbonate → 3-Pyridinecarboxaldehyde, 2-amino-

HRID 1815984Notes

Reaction equation

HRID 1815984 reaction equation
C([NH:7][C:8]1[C:13]([CH:14]=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)(=O)C(C)(C)C.C([O-])([O-])=O.[K+].[K+]>Cl>[NH2:7][C:8]1[C:13]([CH:14]=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

Product 1

HCID 7376333-Pyridinecarboxaldehyde, 2-amino-Yield 101%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Crude 2-(pivaloylamino)-3-pyridinecarboxaldehyde (from step b, 43 g) was dissolved in 3 M HCl (500 mL), and the solution was heated to reflux. After 18 hr the mixture was cooled to RT, and the pH was carefully adjusted to 7 using solid K2CO3. The aqueous solution was extracted with EtOAc (3×500 mL). The combined organic layers were dried (MgSO4)and concentrated to give the title compound (24.57 g, 101%) as a reddish brown solid: 1H NMR (300 MHz, CDCl3) δ 9.85 (s, 1H), 8.24 (m. 1 H), 7.80 (m, 1H), 6.90 (br s, 2H), 6.74 (m, 2H); MS (ES) m/e 123 (M+H)+.

Workup

  1. temperaturethe solution was heated to reflux
  2. extractionThe aqueous solution was extracted with EtOAc (3×500 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ec2b90efbd284b18b8f4858f31b92991
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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