Diethyl Ether → HCID 178507818, compound

HRID 345394Notes

Reaction equation

HRID 345394 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([OH:13])[C:8]([OH:12])=[N:9]2)=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[NH:17]C(OCC)=O.[OH-].[K+].CCOCC>COCCO>[NH2:17][C:3]1[C:4]([N+:14]([O-:16])=[O:15])=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[N:9]=[C:8]([OH:12])[C:7]([OH:13])=[N:6]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 178473438HCID 178473438, compound

Product 1

HCID 178507818HCID 178507818, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 5 g (15,4 mmol) 7-chloro-6-ethoxycarbonylamino-5-nitro-2,3-dihydroxyquinoxaline and 10 g potassium hydroxide in 60 ml 2-methoxyethanol was refluxed for 15 min. After cooling to 25° C., the reaction mixture was added 20 ml 2-methoxyethanol and 40 ml ether. The precipitated black product was filtered off and washed with ether. The crude product was dissolved in 100 ml water. Addition of 4N hydrochloric acid to pH 5-6 gave 3,4 g (87%) 6-amino-7-chloro-5-nitro-2,3-dihydroxyquinoxaline as red crystals, m.p.>300° C. NMR (DMSO-d6) 12.3 (2H, broad m), 7.40 (1H,s), 6.8 (2H, broad s).

Workup

  1. temperaturewas refluxed for 15 min
  2. filtrationThe precipitated black product was filtered off
  3. washwashed with ether
  4. dissolutionThe crude product was dissolved in 100 ml water
  5. additionAddition of 4N hydrochloric acid to pH 5-6

Sources & evidence

ORD record
ord-3b3efcb3040d4fe388db6f17283bdbf9
Source dataset
uspto-grants-1991_10
Patent number
US05057516

Reaction notes

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