Morpholine → 4-(2-Methoxy-4-nitrophenyl)morpholine

HRID 601501노트

반응식

HRID 601501 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18]>>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

참가 물질

3

반응물 2

HCID 8083MorpholineHCID 705192-Chloro-5-nitroanisole

생성물 1

HCID 219364654-(2-Methoxy-4-nitrophenyl)morpholine수율 18.6%

반응 조건

온도
100 °C

실험 절차

Mix morpholine (1.50 mL, 17.20 mmol) and 1-chloro-2-methoxy-4-nitro-benzene (1.06 g, 5.65 mmol) and heat to 100° C. for 4 h while stirring. Cool the solution to room temperature, then partition between EtOAc (40 mL) and 1N HCl (20 mL). Wash the organic solution with water (20 mL) and brine (20 mL), dry, filter, and concentrate. Purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 50% EtOAc/hexanes, to give the title compound as a yellow solid (250 mg, 18%). MS (ES+) 239.0 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 7.86 (dd, 1H, J=8.8, 2.6 Hz), 7.71 (d, 1H, J=2.2 Hz), 6.87 (d, 1H, J=9.2 Hz), 3.94 (s, 31), 3.87 (m, 4H), 3.21 (m, 4H).

후처리

  1. temperatureCool the solution to room temperature
  2. custompartition between EtOAc (40 mL) and 1N HCl (20 mL)
  3. washWash the organic solution with water (20 mL) and brine (20 mL)
  4. customdry
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by flash chromatography

출처 및 근거

ORD 기록
ord-89af306f98ce42e4bf4afca8ac0b3a49
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902356B2

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