Hydrochloric Acid → HCID 178423438, compound

HRID 2398537Notes

Reaction equation

HRID 2398537 reaction equation
O.O.[C:3]([OH:8])(=O)[C:4](O)=[O:5].[C:9]1([CH3:17])[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([NH2:16])[CH:10]=1.C(O)C.Cl>O>[OH:5][C:4]1[C:3]([OH:8])=[N:16][C:11]2[C:12](=[CH:13][CH:14]=[C:9]([CH3:17])[CH:10]=2)[N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 103323,4-DiaminotolueneHCID 61373Oxalic acid dihydrate

Product 1

HCID 178423438HCID 178423438, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of oxalic acid dihydrate (20 g), 3,4-toluenediamine (20 g), ethanol (60 ml), conc. hydrochloric acid (20 ml) and water (50 ml) was refluxed for 5 hours. After cooling to room temperature, the precipitate was removed by filtration, washed with water and dried to yield 27.1g of 2,3-dihydroxy-6-methylquinoxaline, mp> 300° C. Phosgene was bubbled through a mixture of 27.1 g of the 2,3-dihydroxy compound in 200 ml of p-xylene and 5 ml of DMF at 120° C. The solution was degassed with nitrogen, clarified and the solvent flash evaporated to yield 26.2 g of 2,3-dichloro-6-methylquinoxaline, mp 112°-115° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customthe precipitate was removed by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-9c880c9b0d054c309185657a59623d4e
Source dataset
uspto-grants-1977_05
Patent number
US04025510

Reaction notes

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