Phosphorus oxychloride → 8-Nitro-4-oxo-4H-1-benzopyran-2-carbonitrile

HRID 1603882Notes

Reaction equation

HRID 1603882 reaction equation
P(Cl)(Cl)(Cl)=O.[N+:6]([C:9]1[C:18]2[O:17][C:16]([C:19]([NH2:21])=O)=[CH:15][C:14](=[O:22])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([O-:8])=[O:7]>CN(C)C=O>[N+:6]([C:9]1[C:18]2[O:17][C:16]([C:19]#[N:21])=[CH:15][C:14](=[O:22])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 196062688-Nitro-4-oxo-4H-1-benzopyran-2-carboxamide

Product 1

HCID 217112288-Nitro-4-oxo-4H-1-benzopyran-2-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Phosphorous oxychloride (2.86 ml) was added very slowly at 0° C. to dry N,N-dimethylformamide (40 ml) and the mixture was left under stirring at room temperature for 35 minutes. After that a solution of 8-nitro-4-oxo-4H-1-benzopyran-2-carboxamide (1.515 g, 6.47 mmol) in N,N-dimethylformamide (10 ml) was added and the mixture was left under stirring at room temperature for 18 h. After this time, the reaction mixture was poured onto an ice-water mixture (100 ml) and extracted with ethyl acetate (4×40 ml). After drying and removing the solvents under reduced pressure, a residue was obtained which was purified by chromatography through a silica gel column. Eluting with hexane:chloroform, 7:3, 1.094 g of the title product were recovered (78% yield).

Workup

  1. waitthe mixture was left
  2. waitthe mixture was left
  3. stirringunder stirring at room temperature for 18 h
  4. extractionextracted with ethyl acetate (4×40 ml)
  5. customAfter drying
  6. customremoving the solvents under reduced pressure
  7. customa residue was obtained which
  8. customwas purified by chromatography through a silica gel column
  9. washEluting with hexane
  10. customchloroform, 7:3, 1.094 g of the title product were recovered (78% yield)

Sources & evidence

ORD record
ord-5d1ffbb7b0a24dfe8c7b15b2e3af654d
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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