Formic Acid → 8-nitro-2-ethoxycarbonyl-4-oxo-4H-1-benzopyran

HRID 1603880Notes

Reaction equation

HRID 1603880 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7](=[O:16])[C:6]=2[CH:17]=1.C(O)=O>[Pd].CN(C)C=O>[N+:18]([C:4]1[C:5]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7](=[O:16])[C:6]=2[CH:17]=[CH:2][CH:3]=1)([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 19606344ethyl 6-bromo-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylate

Product 1

HCID 100840998-nitro-2-ethoxycarbonyl-4-oxo-4H-1-benzopyranYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of ethyl 6-bromo-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylate (5.0 g, 14.6 mmol), 10% palladium-on-charcoal (0.541 g), formic acid (7.90 ml) and N,N-dimethylformamide (42 ml) was stirred at 145° C. for 5.75 h under inert atmosphere. After this time the mixture was left to cool and the catalyst was removed by filtration, washing it with N,N-dimethylformamide. The resulting filtrate was evaporated to dryness and the obtained residue was purified by chromatography through a silica gel column. Eluting with hexane:chloroform, 85:15, 2.109 g of the title product were recovered (55% yield).

Workup

  1. waitAfter this time the mixture was left
  2. temperatureto cool
  3. customthe catalyst was removed by filtration
  4. washwashing it with N,N-dimethylformamide
  5. customThe resulting filtrate was evaporated to dryness
  6. customthe obtained residue was purified by chromatography through a silica gel column
  7. washEluting with hexane
  8. customchloroform, 85:15, 2.109 g of the title product were recovered (55% yield)

Sources & evidence

ORD record
ord-baf5902e322a4a4eb8fd5975cb730954
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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