Ammonia → HCID 19990452, compound

HRID 346148Notes

Reaction equation

HRID 346148 reaction equation
[C:1]([NH:8][C:9]1[C:10]([N+:19]([O-:21])=O)=[C:11]([C:17]#[N:18])[C:12](=[CH:15][CH:16]=1)[C:13]#[N:14])([C:3](OCC)=[O:4])=[O:2].CN(C)C=O.N>O1CCCC1.[Pt]>[C:13]([C:12]1[C:11]([C:17]#[N:18])=[C:10]2[C:9]([NH:8][C:1](=[O:2])[C:3](=[O:4])[N:19]2[OH:21])=[CH:16][CH:15]=1)#[N:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 14391497HCID 14391497, compound

Product 1

HCID 19990452HCID 19990452, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2 g (0.9 mmol) 4-ethoxalylamino-3-nitrophthalonitrile in 15 ml tetrahydrofuran:dimethylformamide: 25% aqueous ammonia (30:10:0.7) was hydrogenated at atm. pressure by using 25 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. The filtrate was acidified with concentrated hydrochloric acid. The precipitate was filtered off and washed with water, ethanol and ether to give 0.120 g (76%) of 7,8-dicyano-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 7.7 (2H, dd). IR (KBr): 2240 (m). MS (m/e): 228 (M+, 3%), 184 (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-f3cd09f6978341828b44036ec5c1eeaa
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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