Phosphorus oxychloride → HCID 59215152, compound

HRID 2244591Notes

Reaction equation

HRID 2244591 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](O)=[N:7][C:6]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:5][C:4]=2[N:3]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[N:7][C:8]=2[Cl:23])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488437HCID 178488437, compound

Product 1

HCID 59215152HCID 59215152, compoundYield 96.2%

Procedure

2-Chloro-7-(4-methoxyphenyl)-[1,6]naphthyridin-5-ol (135 mg, 0.47 mmol) was dissolved in phosphorus oxychloride (2 mL, 21.5 mmol) and refluxed for 3 hours. An orange solid precipitated. The reaction mixture was diluted with dichloromethane (25 mL) and concentrated to an orange solid. The solid was re-dissolved in EtOAc (300 mL) and washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL) and dried over magnesium sulfate. Filtration and concentration yielded 2,5-dichloro-7-(4-methoxy-phenyl)-[1,6]naphthyridine (138 mg, 86%) as a yellow solid.

Workup

  1. temperaturerefluxed for 3 hours
  2. customAn orange solid precipitated
  3. additionThe reaction mixture was diluted with dichloromethane (25 mL)
  4. concentrationconcentrated to an orange solid
  5. dissolutionThe solid was re-dissolved in EtOAc (300 mL)
  6. washwashed with saturated sodium bicarbonate solution (100 mL), brine (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9ebee5a0504948e8bd0f97950e289dac
Source dataset
uspto-grants-2010_03
Patent number
US07678911B2

Reaction notes

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