Ammonium formate → HCID 22097127, compound

HRID 861511Notes

Reaction equation

HRID 861511 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][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[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][CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22097129HCID 22097129, compound

Product 1

HCID 22097127HCID 22097127, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

36.0 g (0.112 mol) of 6-chloro-1-(2-ethylbutyl)-7-nitro-2,3(1H,4H)-quinoxalinedione were dissolved in 500 ml of isopropanol under nitrogen, and a solution of 70.6 g (1.12 mol) of ammonium formate in 100 ml of water was added. 3.5 g of palladium/carbon (10%) were added and the mixture was refluxed for 1 h. It was subsequently filtered, and the filtrate was concentrated under reduced pressure. The residue was partitioned between aqueous sodium bicarbonate solution and ether. The ether phase was separated off, dried and concentrated under reduced pressure.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationIt was subsequently filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned between aqueous sodium bicarbonate solution and ether
  5. customThe ether phase was separated off
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-680a442d6b6842a0bb438b2dec3a6c40
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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