Tetrahydrofuran → 4-Chloro-N-methyl-3-nitropyridin-2-amine

HRID 1864670노트

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HRID 1864670 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:14]1COCC1>>[Cl:11][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH3:14])[C:7]=1[N+:8]([O-:10])=[O:9]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 40716944-Chloro-3-nitropyridin-2-amine

생성물 1

HCID 249031234-Chloro-N-methyl-3-nitropyridin-2-amine수율 25%

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온도
0 °C

실험 절차

2-Amino-4-chloro-3-nitropyridine (590 mg, 4 mmol) was dissolved in dry THF (15 mL), the solution was cooled to 0° C. and NaH (240 mg, 6 mmol) was added. The reaction mixture was stirred for 2 hours, and allowed to warm at room temperature. The solvent was evaporated and the residue extracted between AcOEt and water. The organic layer was dried (MgSO4) and evaporated. The crude mixture was purified by column chromatography (eluent DCM) to afford the title compound (190 mg, 25%). 1H-NMR (6, ppm, DMSO-d6): 2.88 (d, 3H, Me, J=4.55 Hz), 6.86 (d, 1H, HPy,5, J=5.31 Hz), 7.44 (broad s, 1H, NH), 8.21 (d, 1H, HPy,5, J=5.30 Hz).

후처리

  1. temperatureto warm at room temperature
  2. customThe solvent was evaporated
  3. extractionthe residue extracted between AcOEt and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customThe crude mixture was purified by column chromatography (eluent DCM)

출처 및 근거

ORD 기록
ord-c2c06492e30a4a2eb9ed491907206444
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625922B2

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