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

HRID 1364043Notes

Reaction equation

HRID 1364043 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=O)C>[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 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (31.7 mL, 340 mmol) was added dropwise to a stirred suspension of 3-nitro[1,5]naphthyridine-4-ol (50.0 g, 262 mmol) in 350 mL of DMF that was cooled with a water bath surrounding the reaction vessel. The resulting green suspension was stirred at ambient temperature for 5 hours and poured into 1.5 L of ice water and stirred for an additional hour. The suspension was filtered, washed with water (3×150 mL), and the resulting orange filter cake was dissolved in dichloromethane (800 mL) and washed with saturated aqueous sodium bicarbonate. The layers were separated and the organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 50.49 g of 4-chloro-3-nitro[1,5]naphthyridine as an orange solid.

Workup

  1. temperaturewas cooled with a water bath
  2. stirringstirred for an additional hour
  3. filtrationThe suspension was filtered
  4. washwashed with water (3×150 mL)
  5. dissolutionthe resulting orange filter cake was dissolved in dichloromethane (800 mL)
  6. washwashed with saturated aqueous sodium bicarbonate
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9121ebfddfc84da0ac0e4d84ec9f2fd4
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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