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

HRID 1623091Notes

Reaction equation

HRID 1623091 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18]>>[Cl:3][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526774HCID 178526774, compound

Product 1

HCID 131227874-Chloro-3-nitro-1,5-naphthyridineYield 92.9%

Procedure

Phosphorus oxychloride (38 mL, 408 mmol) was added dropwise over a period of 70 minutes to a stirred suspension of 4-hydroxy-3-nitro[1,5]naphthyridine (60 g, 313.9 mmol). The orange suspension was stirred at ambient temperature for 5 hours and then poured into ice water (1.9 L) and stirred for 30 minutes. The solid was isolated by filtration, washed with water (3×200 mL), and then dissolved in dichloromethane (1.2 L). The solution was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 61.1 g of 4-chloro-3-nitro[1,5]naphthyridine as an orange solid.

Workup

  1. stirringstirred for 30 minutes
  2. customThe solid was isolated by filtration
  3. washwashed with water (3×200 mL)
  4. dissolutiondissolved in dichloromethane (1.2 L)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-940654a6f63c4f2fb9c4394318105aff
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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