Hydrochloric Acid → HCID 178473422, compound

HRID 1461311Notes

Reaction equation

HRID 1461311 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 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-3c904fb25fd54ed4b795919e72210d92
Source dataset
uspto-grants-1991_12
Patent number
US05075306

Reaction notes

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