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

HRID 1187421Notes

Reaction equation

HRID 1187421 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=O)C>[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]naphthyridine

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 DMF (250 mL) at ambient temperature and stirred for 3 hours. 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 to yield 7-bromo-4-chloro-3-nitro[1,5]naphthyridine as a tan solid.

Workup

  1. stirringwith stirring
  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

Sources & evidence

ORD record
ord-c0f304530e724dfd993ef75341d76451
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

Loading…