Phosphorus oxychloride → HCID 86698899, compound

HRID 2174473Notes

Reaction equation

HRID 2174473 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:6]2[C:11]=1[NH:10][C:9](=O)[C:8]([CH3:13])=[CH:7]2.O=P(Cl)(Cl)[Cl:25].[Cl-].C([NH+](CC)CC)C>C(#N)C>[Cl:25][C:9]1[C:8]([CH3:13])=[CH:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 12698378Triethylazanium chlorideHCID 67977265HCID 67977265, compound

Product 1

HCID 86698899HCID 86698899, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

8-chloro-3-methyl-5-(2-(piperidin-1-yl)ethoxy)quinolin-2(1H)-one (160 mg, 0.5 mmol, 1 eq.) was placed in acetonitrile (1.2 mL) in the presence of POCl3 (233 μL, 2.5 mmol, 5 eq.) and triethylammonium chloride (570 mg, 2.5 mmol, 5 eq.). The reaction mixture was stirred at 120° C. during 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 2,8-dichloro-3-methyl-5-(2-(piperidin-1-yl)ethoxy)quinoline (170 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-58aa4384e5c3486889f73f42e6ceec76
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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