Glyoxal → 7-Bromoquinoxalin-5-ol

HRID 525273Notes

Reaction equation

HRID 525273 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][C:3]=1[OH:10].[CH:11]([CH:13]=O)=O>CO>[Br:9][C:5]1[CH:4]=[C:3]([OH:10])[C:2]2[N:1]=[CH:11][CH:13]=[N:8][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 892699422,3-Diamino-5-bromophenol

Product 1

HCID 1366295117-Bromoquinoxalin-5-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As shown in step 6-v of Scheme 6, 2,3-diamino-5-bromophenol (6.0 g, 29.5 mmol) was dissolved in methanol and to this solution was added glyoxal (3.77 g, 2.98 mL, 64.9 mmol) and stirred overnight. The reaction mixture was concentrated under reduced pressure to a minimum volume and the resulting tan solid collected by filtration and dried under high vacuum to produce 7-bromoquinoxalin-5-ol (compound 1017), which was used as is in subsequent reactions without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a minimum volume
  2. filtrationthe resulting tan solid collected by filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-7f92decef4154d75861156ca66c881bc
Source dataset
uspto-grants-2016_05
Patent number
US09340557B2

Reaction notes

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