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

HRID 1815718

반응식

HRID 1815718 반응식
[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

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178487680HCID 178487680, 화합물

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5d211d3a17d3455d8c8c145a43f83c51
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878722B2

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