Phosphorus oxychloride → 4-Chloro-3-nitro-1,5-naphthyridine

HRID 47492Notes

Reaction equation

HRID 47492 reaction equation
P(Cl)(Cl)([Cl:3])=O.[N+:6]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1O)=[N:16][CH:15]=[CH:14][CH:13]=2)([O-:8])=[O:7]>CN(C)C=O>[Cl:3][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[N:11]=[CH:10][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526774HCID 178526774, compound

Product 1

HCID 131227874-Chloro-3-nitro-1,5-naphthyridineYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Phosphorus oxychloride (3.4 mL, 30 mmol) was added to chilled (ice bath) N,N-dimethylformamide (15 mL). The resulting solution was added dropwise to a solution of 3-nitro[1,5]naphthyridin-4-ol (5.73 g, 30 mmol) in N,N-dimethylformamide (35 mL). The reaction mixture was maintained at ambient temperature for 5 hours and then it was poured onto ice. The resulting yellow precipitate was isolated by filtration and then partitioned between dichloromethane (200 mL) and water (150 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and then concentrated under vacuum to provide 4.2 g of crude 4-chloro-3-nitro[1,5]naphthyridine.

Workup

  1. additionit was poured onto ice
  2. customThe resulting yellow precipitate was isolated by filtration
  3. custompartitioned between dichloromethane (200 mL) and water (150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e00c9cd0cc1743e59220754308727e6b
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Reaction notes

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