Hydrochloric Acid → HCID 178473422, compound

HRID 1031096Notes

Reaction equation

HRID 1031096 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([OH:14])=[N:5]2.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>[OH-].[Na+]>[Cl:12][C:11]1[CH:10]=[C:9]2[C:4](=[CH:3][C:2]=1[NH:1][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:5]=[C:6]([OH:14])[C:7]([OH:13])=[N:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 178507221HCID 178507221, compound

Product 1

HCID 178473422HCID 178473422, compoundYield 9,792.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 10 g (47,3 mmol) 6-amino-7-chloro-2,3-dihydroxyquinoxaline in 200 ml 0,5N sodium hydroxide was icecooled, and then 30 ml (0,36 mmol) ethyl chloroformate was added. Stirring was continued at 0° C. for 1 h and at 25° C. for 1 h. To the reaction mixture was added 1N hydrochloric acid to pH 2-3, and the precipitated product was filtered off and washed with water to give 12 g of a crude product. Recrystallization (dimethylsulfoxide-0,5N hydrochloric acid) gave 10 g (75%) 6-chloro-7-ethoxycarbonylamino-2,3-dihydroxyquinoxaline, m.p. >300° C. NMR (DMSO-d6): 11.9 (2H, broad s), 8.9 (1H, broad s), 7.37 (1H,s), 7.17 (1H,s), 4.1 (2H,q), 1.28 (3H,t).

Workup

  1. filtrationthe precipitated product was filtered off
  2. washwashed with water
  3. customto give 12 g of a crude product
  4. customRecrystallization (dimethylsulfoxide-0,5N hydrochloric acid)

Sources & evidence

ORD record
ord-6c9af688d3734f189007902dba8d11aa
Source dataset
uspto-grants-1992_04
Patent number
US05109001

Reaction notes

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