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

HRID 44787Notes

Reaction equation

HRID 44787 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-226e21304d8a467b9fb4109a96de8e01
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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