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

HRID 601501ノート

反応式

HRID 601501 の反応式
[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

参加物

3

反応物 2

HCID 8083MorpholineHCID 705192-Chloro-5-nitroanisole

生成物 1

HCID 219364654-(2-Methoxy-4-nitrophenyl)morpholine収率 18.6%

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-89af306f98ce42e4bf4afca8ac0b3a49
出典データセット
uspto-grants-2011_03
特許番号
US07902356B2

反応ノート

読み込み中…