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

HRID 1990836ノート

反応式

HRID 1990836 の反応式
[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

参加物

5

反応物 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178466714HCID 178466714、化合物

生成物 1

HCID 122934752-chloro-3-ethoxypyridine収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-2946bd3eaef945f7b7678199de872183
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

反応ノート

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