Benzyl Bromide → HCID 9794709, compound

HRID 1387204Notes

Reaction equation

HRID 1387204 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)(O)=[O:2].C([O:24][N:25]1C2C(=CC=C(C(O)=O)C=2)NC(=O)C1=O)C1C=CC=CC=1.C(Br)C1C=CC=CC=1>P([O-])(O)(O)=O.[K+].C(O)C>[OH:14][N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([C:1](=[O:2])[NH:25][OH:24])[CH:13]=2)[NH:8][C:9](=[O:16])[C:10]1=[O:15]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 21715572HCID 21715572, compound

Product 1

HCID 9794709HCID 9794709, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

1-Benzyloxy-7-carboxyquinoxaline-2,3(1H,4H)-dione 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-231ac527d4fa4cd5a578709e536bb58b
Source dataset
uspto-grants-2001_07
Patent number
US06268163B1

Reaction notes

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