N,N-Diethylaniline → 2-chloro-3-ethoxypyridine

HRID 1990836노트

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HRID 1990836 반응식
[CH2:1]([O:3][C:4]1[C:5](O)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:24])=O>O>[Cl:24][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=1

참가 물질

5

반응물 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178466714HCID 178466714, 화합물

생성물 1

HCID 122934752-chloro-3-ethoxypyridine수율 71%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

A mixture of 3-ethoxy-pyridin-2-ol (4.0 g, 28.8 mmol, 1.0 equiv), N,N-diethylaniline (4.61 mL, 4.29 g, 28.8 mmol, 1.0 equiv) and phosphorus oxychloride (2.62 mL, 4.41 g, 28.8 mmol, 1.0 equiv) was heated to 150° C. under microwave irradiation for 20 min. The crude reaction mixture was poured into water (100 mL), the solution adjusted to pH 7 and extracted with dichloromethane (3×100 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (4:1) providing 3.2 g (71%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 3H), 4.12 (q, J=7.0 Hz, 2H), 7.18 (d, J=3.2 Hz, 2H), 7.98 (t, J=3.2 Hz, 1H). MS (ISP): 157.7 [M+H]+.

후처리

  1. customThe crude reaction mixture
  2. extractionextracted with dichloromethane (3×100 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent removed by evaporation under reduced pressure
  5. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-2946bd3eaef945f7b7678199de872183
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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