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

HRID 487381Notes

Reaction equation

HRID 487381 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 was 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 was 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-192de370f669496eb461be80efd6b0ee
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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