Dimethylformamide → HCID 19990429, compound

HRID 346154Notes

Reaction equation

HRID 346154 reaction equation
[C:1]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]N)=[CH:11][C:10]=1[N+:17]([O-:19])=O)([C:3]([O:5]CC)=O)=[O:2].[CH3:20][N:21](C)C=O>>[C:20]([CH2:13][C:12]1[CH:11]=[C:10]2[C:9]([NH:8][C:1](=[O:2])[C:3](=[O:5])[N:17]2[OH:19])=[CH:16][CH:15]=1)#[N:21]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 19990471HCID 19990471, compound

Product 1

HCID 19990429HCID 19990429, compoundYield 82%

Procedure

A solution of 1.0 g (3.6 mmol) 4-ethoxalylamino-3-nitrobenzylamine in 30 ml dimethylformamide was hydrogenated at atm. pressure by using 100 mg 5% Pt-c as a catalyst. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was stirred with water and the precipitate was filtered off. The product was washed with water and 5 ml ethanol to give 0.64 g (82%) of 7-cyanomethyl-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 12,3 (1H, broad s), 7.6-7.3 (3H, m), 4.2 (2H, s). IR (KBr): 2250 cm-1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. filtrationthe precipitate was filtered off
  4. washThe product was washed with water and 5 ml ethanol

Sources & evidence

ORD record
ord-c10e17994eef4178847f93d10767e1c1
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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