Hydrochloric Acid → HCID 178473422, compound

HRID 345392Notes

Reaction equation

HRID 345392 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.[OH-].[Na+].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].Cl>>[Cl:12][C:11]1[CH:10]=[C:9]2[C:4](=[CH:3][C:2]=1[NH:1][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:5]=[C:6]([OH:14])[C:7]([OH:13])=[N:8]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 178507221HCID 178507221, compound

Product 1

HCID 178473422HCID 178473422, compoundYield 9,792.4%

Procedure

A solution of 10 g (47,3 mmol) 6-amino-7-chloro-2,3-dihydroxyquinoxaline in 200 ml O,5N sodium hydroxide was ice-cooled, 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. temperaturecooled
  2. filtrationthe precipitated product was filtered off
  3. washwashed with water
  4. customto give 12 g of a crude product
  5. customRecrystallization (dimethylsulfoxide-0,5N hydrochloric acid)

Sources & evidence

ORD record
ord-d0b07101c5714a08a1a60de1cc4900ca
Source dataset
uspto-grants-1991_10
Patent number
US05057516

Reaction notes

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