Diethyl Ether → HCID 178507818, compound

HRID 1031098Notes

Reaction equation

HRID 1031098 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-64143e0fa0a94eb5a5001a3bb958c06d
Source dataset
uspto-grants-1992_04
Patent number
US05109001

Reaction notes

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