Phosphorus oxychloride → HCID 86698898, compound

HRID 2174467Notes

Reaction equation

HRID 2174467 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:6]2[C:11]=1[NH:10][C:9](=O)[CH:8]=[CH:7]2.O=P(Cl)(Cl)[Cl:24].[Cl-].C([NH+](CC)CC)C>C(#N)C>[Cl:24][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 12698378Triethylazanium chlorideHCID 67976269HCID 67976269, compound

Product 1

HCID 86698898HCID 86698898, compoundYield 119.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

8-chloro-5-(2-morpholinoethoxy)quinolin-2(1H)-one (200 mg, 0.6 mmol, 1 eq.) was placed in acetonitrile (1.7 mL) in the presence of POCl3 (301 μL, 3.2 mmol, 5 eq.) and triethylammonium chloride (738 mg, 3.2 mmol, 5 eq.). The reaction mixture was stirred at 120° C. for 3 hours. The mixture was then concentrated under reduced pressure and, after adding water to the residue (5 mL), was stirred at room temperature during 30 minutes. Then the resulting precipitate was washed with water and filtered to give 4-(2-((2,8-dichloroquinolin-5-yl)oxy)ethyl)morpholine (234 mg, 100%).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionafter adding water to the residue (5 mL)
  3. stirringwas stirred at room temperature during 30 minutes
  4. washThen the resulting precipitate was washed with water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e850721ad2044579aaffd05d35afc81f
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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