Phosphorus oxychloride → 3-Bromo-8-chloro-1,5-naphthyridine

HRID 503500Notes

Reaction equation

HRID 503500 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[CH:7][CH:8]=[N:9]2)=[N:4][CH:3]=1.P(Cl)(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][C:6]=2[Cl:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516370HCID 178516370, compound

Product 1

HCID 134591373-Bromo-8-chloro-1,5-naphthyridine

Procedure

7-Bromo-1,5-naphthyridin-4-ol (7.0 g) and phosphoryl chloride (200 mL) were refluxed for 5 h in a RBF fitted with a reflux condenser. Excess POCl3 was distilled off under reduced pressure and the residue poured onto ice. This cold mixture was carefully neutralized with aq. ammonia, which caused an exotherm. The resulting solid was filtered, washed with water and dried. The product was recrystallized from n-heptane to give white needles of 3-bromo-8-chloro-1,5-naphthyridine.

Workup

  1. customfitted with a reflux condenser
  2. distillationExcess POCl3 was distilled off under reduced pressure
  3. additionthe residue poured onto ice
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customdried
  7. customThe product was recrystallized from n-heptane

Sources & evidence

ORD record
ord-e296dcb8650c428f8197ba3b5548c502
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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