Phosphorus oxychloride → 4-Chloro-7-methoxy-2-(pyridin-2-yl)quinoline

HRID 1815718ノート

反応式

HRID 1815718 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](O)=[CH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:10]2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:8]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178487680HCID 178487680、化合物

生成物 1

HCID 222502394-Chloro-7-methoxy-2-(pyridin-2-yl)quinoline

実験手順

A mixture of 7-Methoxy-2-pyridin-2-yl-quinolin-4-ol (2.2 g, 8.71 mmol) in POCl3 (92 mL) was refluxed for 3 h and then removed the solvent in vacuo. Ice water was added to the residue, adjusted the pH>10 with 1.0 N NaOH, and extrated with EtOAc (2×). The combined extract was washed with water, brine, dried (MgSO4), removed solvent to supply the product as a yellow solid (89%, 2.1 g): DMSO-D6) δ ppm 3.97 (s, 3H), 7.40 (dd, J=9.16, 2.44 Hz, 1H), 7.53 (m, 1H), 8.01 (m, 1H), 8.09 (d, J=9.16 Hz, 1H), 8.46 (s, 1H), 8.56 (d, J=7.93 Hz, 1H), 8.74 (d, J=3.97 Hz, 1H). LC-MS (retention time: 1.50, Method D), MS m/z 271 (M++1).

後処理

  1. temperaturewas refluxed for 3 h
  2. customremoved the solvent in vacuo
  3. additionIce water was added to the residue
  4. extractionThe combined extract
  5. washwas washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customremoved solvent to supply the product as a yellow solid (89%, 2.1 g)

出典と根拠

ORDレコード
ord-5d211d3a17d3455d8c8c145a43f83c51
出典データセット
uspto-grants-2005_04
特許番号
US06878722B2

反応ノート

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