Phosphorus oxychloride → HCID 17894863, compound

HRID 1892253Notes

Reaction equation

HRID 1892253 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=O)[CH:3]=1.O=P(Cl)(Cl)[Cl:15]>C1(C)C=CC=CC=1>[Cl:15][C:4]1[CH:3]=[C:2]([CH3:1])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1415873HCID 1415873, compound

Product 1

HCID 17894863HCID 17894863, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-methyl-1,8-naphthyridin-2(1H)-one (440 mg, 2.75 mmol) in toluene was added 302 uL of POCl3 (1.2 eq). The resulting mixture was refluxed at 120° C. for 3 hours. After cooling to room temperature the reaction mixture was quenched into ice-H2O and extracted with EtOAc (3×10 mL). The combined organic extracts was washed with H2O (2×15 mL), brine (1×20 mL), and then dried over MgSO4. Concentration and purification by MPLC gave the desired 2-chloro-4-methyl-1,8-naphthyridine (330 mg, 67%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.72 (s, 3 H) 7.35 (d, J=1.17 Hz, 1 H) 7.53 (dd, J=8.20, 4.40 Hz, 1 H) 8.36 (dd, J=8.35, 1.90 Hz, 1 H) 9.10 (dd, 1 H).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas quenched into ice-H2O
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined organic extracts was washed with H2O (2×15 mL), brine (1×20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationConcentration and purification by MPLC

Sources & evidence

ORD record
ord-d3c2adf5259e42f2a723d8dff5775774
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

Loading…