Phosphorus oxychloride → HCID 86690693, compound

HRID 711369Notes

Reaction equation

HRID 711369 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2O.P(Cl)(Cl)([Cl:18])=O>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Cl:18])[C:6]([N+:12]([O-:14])=[O:13])=[CH:7][N:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526765HCID 178526765, compound

Product 1

HCID 86690693HCID 86690693, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 6-chloro-3-nitro-1,5-naphthyridin-4-ol (5 g, 22.1 mmol) in 15 mL of DMF, was added a solution of phosphorous oxychloride (2.7 mL, 28.8 mmol) in anhydrous DMF (10 mL) over 3 min. The mixture was stirred at room temperature overnight. The mixture was then poured onto crushed ice. The resulting precipitate was collected by filtration, washed with H2O, and dried in vacuo to afford 2,8-dichloro-7-nitro-1,5-naphthyridine as yellow solid (4 g, yield 74.0%). MS (m/z): 244 (M+H)+.

Workup

  1. additionThe mixture was then poured
  2. customonto crushed ice
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7ba676236a764fcbbdbfe85641ee3b2d
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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