Phosphorus oxychloride → 2-Chloro-1,8-naphthyridine

HRID 707215

Reaction equation

HRID 707215 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH:4]=[CH:3][C:2]=1O.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515637HCID 178515637, compound

Product 1

HCID 51528382-Chloro-1,8-naphthyridine

Procedure

1,8-Naphthyridin-2-ol (2.80 g, 19.16 mmol) was suspended in phosphorus oxychloride (100 ml, 1092 mmol) and heated at gentle reflux. The chlorination was followed by LC/MS and once the conversion was complete the reaction was evaporated to dryness and the residue partitioned between water (400 mL) and ethyl acetate (2×400 mL). The aqueous was extracted with additional ethyl acetate (2×400 mL). The combined organic layers were dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude compound was used without further purification.

Workup

  1. temperatureheated at gentle reflux
  2. customwas evaporated to dryness
  3. customthe residue partitioned between water (400 mL) and ethyl acetate (2×400 mL)
  4. extractionThe aqueous was extracted with additional ethyl acetate (2×400 mL)
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe crude compound was used without further purification

Sources & evidence

ORD record
ord-4298614be6074d24adcb8a43ac2001c0
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Linked notes

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