Benzyl Bromide → HCID 18415564, compound

HRID 990592Notes

Reaction equation

HRID 990592 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([NH:8][C:9](=[O:16])[C:10](=[O:15])[N:11]2[OH:14])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>P([O-])(O)(O)=O.[K+].C(O)C>[CH2:17]([O:14][N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:13]=2)[NH:8][C:9](=[O:16])[C:10]1=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 18415566HCID 18415566, compound

Product 1

HCID 18415564HCID 18415564, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

7-Carboxy-1-hydroxyquinoxaline-2,3(1H,4H)-dione (2.22 g, 10 mmol) was dissolved in a mixture of 50 ml of 1M potassium dihydrogen phosphate buffer (pH 7.4) and 25 ml of ethanol by gently heating. To the cooled mixture was added 1.19 ml (10 mmol) of benzylbromide and the mixture was stirred overnight at room temperature. The precipitate was isolated by filtration and washed with ethanol. The crude product was triturated with 4M hydrochloric acid and washed with water and dried in vacuo to give 1.56 g (50%) of the title compound. 1H-NMR (DMSO-d6): 5.22 (s, 2H, CH2), 7.2-7.9 (m, 8H, ArH), 12.35 (s, 1H, exchangeable), 13.05 (br.s, 1H, exchangeable).

Workup

  1. temperatureby gently heating
  2. customThe precipitate was isolated by filtration
  3. washwashed with ethanol
  4. customThe crude product was triturated with 4M hydrochloric acid
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5bc86cb897c249239b7c42e045d6db8b
Source dataset
uspto-grants-2002_10
Patent number
US06461610B1

Reaction notes

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