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

HRID 895670노트

반응식

HRID 895670 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]

후처리

  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

출처 및 근거

ORD 기록
ord-5f56aad308da4de588df9844fa521ff8
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916827B2

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