Phosphorus oxychloride → HCID 58289568, compound

HRID 1422535Notes

Reaction equation

HRID 1422535 reaction equation
[Cl:1][C:2]1[C:3]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[N:13]=1)[CH:8]=[C:7]2O.O=P(Cl)(Cl)[Cl:29]>>[Cl:29][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[C:3]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[N:13]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178496096HCID 178496096, compound

Product 1

HCID 58289568HCID 58289568, compound

Conditions

Temperature
85 °C

Procedure

8-Chloro-2-(6-isopropyl-pyridin-2-yl)-7-(2-methoxy-ethoxy)-quinolin-4-ol (2.16 g, 5.8 mmol) was dissolved in POCl3 (20 mL) under an atmosphere of nitrogen. The reaction was heated to 85° C. for 4 hours. The reaction was cooled to 0° C. and quenched with water. A saturated solution of sodium bicarbonate in water was used to neutralize the reaction. The reaction was extracted with ethyl acetate. The organic layer was dried with sodium sulfate, filtered and was concentrated. 4,8-Dichloro-2-(6-isopropyl-pyridin-2-yl)-7-(2-methoxy-ethoxy)-quinoline (1.87 g, 82%) was purified by silica gel chromatography.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with water
  3. customthe reaction
  4. extractionThe reaction was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationwas concentrated
  8. custom4,8-Dichloro-2-(6-isopropyl-pyridin-2-yl)-7-(2-methoxy-ethoxy)-quinoline (1.87 g, 82%) was purified by silica gel chromatography

Sources & evidence

ORD record
ord-13acfcd97e814e21a03291ee02b44dd8
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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