Sodium Carbonate → 4-Chloro-7-methoxy-1,6-naphthyridine

HRID 1013630Notes

Reaction equation

HRID 1013630 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH:8]=[CH:9][NH:10]2)=[CH:5][N:4]=1.C(=O)([O-])[O-].[Na+].[Na+].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 534871227-Methoxy-1H-1,6-naphthyridin-4-one

Product 1

HCID 594273184-Chloro-7-methoxy-1,6-naphthyridine

Procedure

A two neck RBF equipped with CaCl2 guard tube was charged with 7-Methoxy-1H-[1,6]naphthyridin-4-one (28 g, 159 mmol) and POCl3(280 mL). The reaction mixture was stirred at RT for 3 h. The reaction mixture was poured into ice water and the pH was carefully adjusted to 8 with solid sodium carbonate (highly exothermic reaction). The product was extracted with EtOAc. The combined organic layer was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel (230-400 mesh) eluting with ethyl acetate hexane mixture.

Workup

  1. customA two neck RBF equipped with CaCl2 guard tube
  2. customhighly exothermic reaction)
  3. extractionThe product was extracted with EtOAc
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel (230-400 mesh)
  8. washeluting with ethyl acetate hexane mixture

Sources & evidence

ORD record
ord-dda3d4c687a4436a892cb1a6809e371a
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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