Methanol → HCID 178497040, compound

HRID 259514Notes

Reaction equation

HRID 259514 reaction equation
[CH3:1][C:2]1[N+:11]([O-:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N+:4]([O-:13])[C:3]=1[C:14]([O:16][CH3:17])=[O:15].[Br:18]Br.CO>CN(C)C=O>[Br:18][CH2:1][C:2]1[N+:11]([O-:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N+:4]([O-:13])[C:3]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 178498463HCID 178498463, compound

Product 1

HCID 178497040HCID 178497040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-methyl-2-quinoxalinecarboxylate-1,4-dioxide (1.2 moles) were suspended in 475 ml of dimethylformamide and 64 ml of bromine was added dropwise with stirring over 1.5 hours while the temperature rose to 42° C. After additional stirring for 48 hours 1.5 liters of methanol were added and stirred for about 1/2 hour. The precipitated product was removed by filtration, washed with water and dried. Yield, 251 grams (68%); m.p. 113°-16° C.

Workup

  1. customrose to 42° C
  2. additionwere added
  3. stirringstirred for about 1/2 hour
  4. customThe precipitated product was removed by filtration
  5. washwashed with water
  6. customdried
  7. customYield

Sources & evidence

ORD record
ord-6e2c8ee2721f42699ae525f308206ba4
Source dataset
uspto-grants-1977_07
Patent number
US04038392

Reaction notes

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