Acetic Anhydride → 4-Acetylamino-2,6-diethylpyridine-3-carboxaldehyde

HRID 1587501Notes

Reaction equation

HRID 1587501 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=[O:13].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([NH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=[O:13])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 190937814-Amino-2,6-diethyl-pyridine-3-carbaldehyde

Product 1

HCID 190937624-Acetylamino-2,6-diethylpyridine-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-amino-2,6-diethylpyridine-3-carbaldehyde (2.0 g) and acetic anhydride (10 ml) in pyridine (20 ml) was heated at reflux for 3 hours. Volatile material was removed by evaporation and the residue was dissolved in ethyl acetate. The solution as washed with aqueous sodium carbonate solution, followed by saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation to give an oil which was purified by flash chromatography, eluting with ethyl acetate/petroleum ether (1:1 v/v) to give 4-acetylamino-2,6-diethylpyridine-3-carboxaldehyde as a yellow solid (0.9 g); m.p. 91°-92° C.; NMR (CDCl3): 1.3(t, 3H), 1.35(t, 3H), 2.26(s, 3H), 2.8(q, 2H), 3.14(q, 2H), 8.38(s, 1H), 10.4(s, 1H), 11.7(broad, 1H); mass spectrum (CI): 221 (M+H)+ ; microanalysis, found: C, 65.3; H, 7.3; N, 12.3%; C12H16N2O2 requires: C, 65.4; H, 7.3; N, 12.7%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customVolatile material was removed by evaporation
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution as washed with aqueous sodium carbonate solution
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customto give an oil which
  9. customwas purified by flash chromatography
  10. washeluting with ethyl acetate/petroleum ether (1:1 v/v)

Sources & evidence

ORD record
ord-984c0fe5ae8b46d6a82106c79b08f6c2
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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