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

HRID 1815718

Reaction equation

HRID 1815718 reaction equation
[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

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487680HCID 178487680, compound

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5d211d3a17d3455d8c8c145a43f83c51
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Linked notes

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