Phosphorus oxychloride → 2-Chloro-6-methoxyquinoxaline

HRID 250036

반응식

HRID 250036 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[N:6]2.COC1C=C2C(N=CC(=O)N2)=CC=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:8]1[CH:7]=[N:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

참가 물질

4

반응물 3

HCID 24813Phosphorus oxychlorideHCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneHCID 134377076-Methoxyquinoxalin-2(1H)-one

생성물 1

HCID 126864122-Chloro-6-methoxyquinoxaline수율 35%

실험 절차

A mixture of 6-methoxyquinoxalin-2(1H)-one and 7-methoxyquinoxalin-2(1H)-one (5.67 g, 32.20 mmol) was refluxed in phosphorus oxychloride (120 mL) for 1 h. The reaction was concentrated and quenched by addition of ice, then basified with sodium carbonate, and extracted with ethyl acetate (3×200 mL). The organic layers were combined and concentrated in vacuo. The crude product was absorbed onto sodium sulfate and purified by column chromatography (0 to 5% ethyl acetate/hexanes) to afford 2-chloro-6-methoxyquinoxaline (2.21 g, 11.36 mmol, 35% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.69 (s, 1 H), 7.88 (d, J=9.32 Hz, 1 H), 7.43 (dd, J=9.32, 2.77 Hz, 1 H), 7.37 (d, J=2.77 Hz, 1 H), 3.95 (s, 3 H).

후처리

  1. concentrationThe reaction was concentrated
  2. customquenched by addition of ice
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was absorbed onto sodium sulfate
  6. custompurified by column chromatography (0 to 5% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-25e0870ba1884210bdecf6b3e8813416
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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