Ammonium formate → HCID 22097155, compound

HRID 1457564Notes

Reaction equation

HRID 1457564 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7](=[O:21])[C:6](=[O:22])[NH:5]2.C([O-])=O.[NH4+]>C(O)(C)C.O.[Pd]>[NH2:12][C:11]1[CH:10]=[C:9]2[C:4]([NH:5][C:6](=[O:22])[C:7](=[O:21])[N:8]2[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22097123HCID 22097123, compound

Product 1

HCID 22097155HCID 22097155, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

84.3 g (0.26 mol) of 6-chloro-1-(ethoxycarbonylmethyl)-7-nitroquinoxaline-2,3(1H,4H)-dione were suspended in 1.5 l of isopropanol and successively 194.2 g (3.1 mol) of ammonium formate dissolved in 500 ml of water, and 8.5 g of palladium/carbon (10%) were added. The mixture was then heated at 75° C. for 4 h and, after cooling, filtered, and the filter cake was extracted three times with 800 ml of dimethylformamide. The combined dimethylformamide phases were concentrated under reduced pressure, and the residue was washed with water. 53.2 g (79%) of the product were obtained.

Workup

  1. temperatureafter cooling
  2. filtrationfiltered
  3. extractionthe filter cake was extracted three times with 800 ml of dimethylformamide
  4. concentrationThe combined dimethylformamide phases were concentrated under reduced pressure
  5. washthe residue was washed with water

Sources & evidence

ORD record
ord-587ab9e4f4d14145af81115f62dff58f
Source dataset
uspto-grants-1998_12
Patent number
US05849743

Reaction notes

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