Sodium Methoxide → 4-Methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine

HRID 1191214노트

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HRID 1191214 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]([NH2:18])[C:3]=1[N+:19]([O-:21])=[O:20].[CH3:22][O-:23].[Na+]>CO.O>[CH3:22][O:23][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]([NH2:18])[C:3]=1[N+:19]([O-:21])=[O:20]

참가 물질

5

반응물 2

HCID 10942334Sodium MethoxideHCID 674111324-Chloro-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine

생성물 1

HCID 674106994-Methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
70 °C

실험 절차

To a solution of 4-chloro-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine (317 mg, 0.998 mmol, prepared as described in the Example 1) in MeOH (5 mL) was added NaOMe (1.99 mL, 0.998 mmol, 0.5 M solution in MeOH). The resulting mixture was stirred at 70° C. overnight. The reaction mixture was then diluted with water (20 mL) and extracted with EtOAc (3×10 mL). The organic layers were combined, dried (MgSO4) and concentrated. The resulting residue was purified on silica 0:100-50:50 EtOAc-hexanes to yield 4-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine. 1H-NMR (400 MHz, CDCl3) δ: 7.78 (d, J=7.8 Hz, 1H), 7.61-7.67 (m, 1H), 7.54-7.60 (m, 1H), 7.50 (d, J=7.6 Hz, 1H), 6.46 (s, 1H), 6.27 (br. s., 2H), 3.97 (s, 3H).

후처리

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting residue was purified on silica 0:100-50:50 EtOAc-hexanes

출처 및 근거

ORD 기록
ord-02042db24a824613ba96ab58ce6c9232
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680098B2

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