Ethylamine → N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amine

HRID 895670Notes

Reaction equation

HRID 895670 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[CH:9]=[N+:10]([O-:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].[CH2:18]([NH:20]CC)[CH3:19].C(N)C>C1COCC1>[CH2:18]([NH:20][C:8]1[CH:9]=[N+:10]([O-:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH3:19]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 5998173-Chloro-4-nitropyridine N-oxide

Product 1

HCID 12343672N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous K2CO3 (19 g, 144.5 mmol) is suspended in a solution of 3-chloro-4-nitro-pyridine-1-oxide (10 g, 57.8 mmol) in anhydrous acetonitrle (100 mL). Excess diethyl amine (2.0 M) in THF is added to the above suspension with ice-bath cooling. After complete addition of ethylamine, the reaction mixture is allowed to warm to room temperature and stir overnight. The reaction mixture is filtered to remove K2CO3 and the filtrate is evaporated under reduced pressure to remove volatile solvents. The organic residue is subjected to chromatography eluting with 30% EtOAc-hexanes to afford 3-ethylamino-4-nitro-pyridine-1-oxide as an orange solid (8.2 g); 1H NMR (300 MHz, CDCl3): δ 8.0 1 (d, J=7.5 Hz, 1H), 7.91(s, 1H), 7.8 (brs, NH), 7.44 (d, J=7.2 Hz, 1H), 3.30 (t, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), m/z 184 [M+1]

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture is filtered
  3. customto remove K2CO3
  4. customthe filtrate is evaporated under reduced pressure
  5. customto remove volatile solvents
  6. washeluting with 30% EtOAc-hexanes

Sources & evidence

ORD record
ord-5f56aad308da4de588df9844fa521ff8
Source dataset
uspto-grants-2005_07
Patent number
US06916827B2

Reaction notes

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