Phosphorus oxychloride → 7-Bromo-4-chloro-3-nitro[1,5]naphthyridine

HRID 1469328Notes

Reaction equation

HRID 1469328 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](O)=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[N:14]2)=[N:9][CH:8]=1>CN(C)C=O>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([Cl:3])=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[N:14]2)=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526758HCID 178526758, compound

Product 1

HCID 574578377-Bromo-4-chloro-3-nitro[1,5]naphthyridineYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorous oxychloride (24 mL, 257.7 mmol) was added slowly dropwise to a 0° C. suspension of 7-bromo-3-nitro[1,5]naphthyridin-4-ol (60.00 g, 222.2 mmol) in N,N-dimethylformamide (DMF; 410 mL), maintaining the temperature below 10° C. After addition was completed, the reaction was allowed to warm to ambient temperature over a 3 hour period. The reaction mixture was then added to ice water (1700 mL) with stirring. A solid precipitate formed, which was isolated by vacuum filtration and rinsed with water. The material was partitioned between chloroform (3 Liters) and saturated aqueous sodium bicarbonate (300 mL). The organic phase was isolated, dried over anhydrous sodium sulfate, then concentrated under reduced pressure to yield 54.42 g of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine as short, off-white needles.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. additionAfter addition
  3. customA solid precipitate formed
  4. customwhich was isolated by vacuum filtration
  5. washrinsed with water
  6. customThe material was partitioned between chloroform (3 Liters) and saturated aqueous sodium bicarbonate (300 mL)
  7. customThe organic phase was isolated
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-789d1869ac1a4ee2b3d7cbdce2aa61e9
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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