Isopropanol → HCID 22097155, compound

HRID 1458865Notes

Reaction equation

HRID 1458865 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)(C)C.C([O-])=O.[NH4+]>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 3

HCID 3776IsopropanolHCID 2723923Ammonium formateHCID 22097123HCID 22097123, compound

Product 1

HCID 22097155HCID 22097155, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

84.3 g (0.26 mol) of 6-chloro-1-(ethoxy-carbonylmethyl)-7-nitro-2,3(1H,4H)-quinoxalinedione were suspended in 1.5 1 of isopropanol, and 194.2 g (3.1 mol) of ammonium formate dissolved in 500 ml of water, and 8.5 g of palladium/carbon (10%) were successively added. The mixture was 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 to yield 53.2 g (79%) of the product.

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-bc22b685b44041fbbbdf021445749eb9
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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