Diethyl Ether → HCID 178507818, compound

HRID 1110746Notes

Reaction equation

HRID 1110746 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-2e6c953e2c1b4818b6fb48cf5bf93089
Source dataset
uspto-grants-1990_12
Patent number
US04977155

Reaction notes

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