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

HRID 909350Notes

Reaction equation

HRID 909350 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 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorous oxychloride (16.76 g, 10.19 mL, 109.3 mmol) was added slowly dropwise to a suspension of 7-bromo-3-nitro[1,5]naphthyridin-4-ol (21.09 g, 78.1 mmol) in N,N-dimethylformamide (250 mL) (DMF) at ambient temperature and maintained overnight. The reaction mixture was then added to ice water (400 mL) with stirring. A solid precipitate formed, which was isolated by vacuum filtration and washed with water. The material was dried under high vacuum at ambient temperature overnight to yield 20.79 g of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine as a tan solid.

Workup

  1. temperaturemaintained overnight
  2. customA solid precipitate formed
  3. customwhich was isolated by vacuum filtration
  4. washwashed with water
  5. customThe material was dried under high vacuum at ambient temperature overnight

Sources & evidence

ORD record
ord-52f0d1afefa54ae3a8a3c7c9e57de8d5
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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