Ammonia → HCID 19990430, compound

HRID 346146Notes

Reaction equation

HRID 346146 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]([F:22])([F:21])[F:20])[C:10]=1[N+:23]([O-])=[O:24])([C:3]([O:5]CC)=O)=[O:2].CN(C)C=O.N>O1CCCC1.[Pd]>[F:16][C:15]([F:17])([F:18])[C:13]1[CH:14]=[C:9]2[C:10](=[C:11]([C:19]([F:20])([F:21])[F:22])[CH:12]=1)[N:23]([OH:24])[C:3](=[O:5])[C:1](=[O:2])[NH:8]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 86745190HCID 86745190, compound

Product 1

HCID 19990430HCID 19990430, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.20 g (0.5 mmol) N-ethoxalyl-3,5-bistrifluoromethyl-2-nitroaniline in 10 ml tetrahydrofuran:dimethylformamide:25% aqueous ammonia (30:10:0.7) was hydrogenated at atm. pressure by using 5% Pd-C (0.02 g) as a catalyst. The reaction mixture was filtered and evaporated in vacuo. The residue was stirred with water, and the precipitate was filtered off to give 0.11 g (84%) of 6,8-bistrifluoromethyl-1-hydroxyquinoxaline- 2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 8.1 (s). MS (m/e): 314 (M+, 40%), 173 (45%), 69 (100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-9a635824bb904c67aebce3eff53fca18
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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