Ammonia → HCID 19990446, compound

HRID 346150Notes

Reaction equation

HRID 346150 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=O)[CH:3]=1.CN(C)[CH:15]=[O:16].N.[O:19]1CCC[CH2:20]1>[Pt]>[CH3:9][C:8]1[CH:7]=[C:5]2[C:4](=[CH:3][C:2]=1[CH3:1])[N:10]([OH:12])[C:20](=[O:19])[C:15](=[O:16])[NH:6]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 814454,5-Dimethyl-2-nitrobenzenamine

Product 1

HCID 19990446HCID 19990446, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

1.0 g (3.8 mmol) 4,5-dimethyl-2-nitroaniline in 30 ml tetrahydrofuran:dimethylformamide: 25% aqueous ammonia (30:10:0.7) was hydrogenated at atm. pressure by using 60 mg 5% Pt-C as a catalyst. The precipitate was filtered off and washed with tetrahydrofuran. The filter cake was washed several times with 1N aqueous potassium hydroxide, and the filtrate was acidified with concentrated hydrochloric acid. The precipitate was filtered off and washed with water, ethanol and ether to give 0.13 g (17%) of 6,7-dimethyl-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 11.9 (1H, broad s), 7.3 (1H, s), 7.0 (1H, s), 2.3 (6H, s). MS (m/e): 206 (M+, 70%), 161 (100%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with tetrahydrofuran
  3. washThe filter cake was washed several times with 1N aqueous potassium hydroxide
  4. filtrationThe precipitate was filtered off
  5. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-642899324be94c6e8ff29bed9844da38
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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