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

HRID 1988727Notes

Reaction equation

HRID 1988727 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]>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

5

Reactant 3

HCID 8021Diethylamine2×HCID 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 under cold conditions (ice-bath). After complete addition of diethyl amine, the reaction mixture is allowed to warm to room temperature and left stirring overnight. The reaction mixture is filtered to remove K2CO3 and the filtrate 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. 1H NMR (300 MHz, CDCl3): δ8.0 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. waitleft
  2. filtrationThe reaction mixture is filtered
  3. customto remove K2CO3
  4. customthe filtrate evaporated under reduced pressure
  5. customto remove volatile solvents
  6. washeluting with 30% EtOAc-hexanes

Sources & evidence

ORD record
ord-851b7340e32d4bf8aa7615acea0a8950
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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