Butanedione → HCID 178432086, compound

HRID 345407Notes

Reaction equation

HRID 345407 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([OH:14])[C:6]([OH:13])=[N:7]2.[CH3:15][C:16](=O)[C:17](=O)[CH3:18]>O>[OH:14][C:5]1[C:6]([OH:13])=[N:7][C:8]2[C:3]([N:4]=1)=[C:2]1[C:11](=[CH:10][CH:9]=2)[N:12]=[C:17]([CH3:18])[C:16]([CH3:15])=[N:1]1

Participants

4

Reactant 2

HCID 650ButanedioneHCID 178507339HCID 178507339, compound

Product 1

HCID 178432086HCID 178432086, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 0,5 g (2,6 mmol) 5,6-diamino-2,3-dihydroxyquinoxaline and 10 ml water was at 50° C. added a solution of 0,45 g (5,2 mmol) 2,3-butanedione in 5 ml water. The reaction mixture was stirred at 50° for 4 h. After cooling to 25° C., the precipitate was filtered off and washed with water. The crude product was dissolved in 2N sodium hydroxide and reprecipitated with 2N hydrochloric acid to pH 6-7 to give 0,4 g (64%) 2,3-dihydroxy-8,9-dimethylpyrazino(2,3-f)quinoxaline, m.p.>300° C. NMR (DMSO-d6): 7.27 (1H,d), 6.93 (1H,d), 2.07 (6H,s).

Workup

  1. customwas at 50° C.
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. dissolutionThe crude product was dissolved in 2N sodium hydroxide
  5. customreprecipitated with 2N hydrochloric acid to pH 6-7

Sources & evidence

ORD record
ord-2f0023d59de244358c4e49204bfca5ba
Source dataset
uspto-grants-1991_10
Patent number
US05057516

Reaction notes

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