Hydrochloric Acid → 6-Bromo-1-carboxymethylquinoxaline-2,3(1H,4H)-dione

HRID 373772Notes

Reaction equation

HRID 373772 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]CC)=[O:14])[C:7](=[O:18])[C:6](=[O:19])[NH:5]2.[OH-].[Na+].Cl>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7](=[O:18])[C:6](=[O:19])[NH:5]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 198084556-Bromo-1-ethoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 198084436-Bromo-1-carboxymethylquinoxaline-2,3(1H,4H)-dioneYield 70.2%

Procedure

The ester of example 2 (0.33 g, 1 mmol) was reacted with 4% NaOH (9 ml) for 3 h at room temperature. The mixture was cooled in an ice bath and the pH was adjusted to 1 with 4M hydrochloric acid. The precipitate was filtered off, washed with water and recrystallized from acetic acid to afford 0.21 g (70%) of the title compound. M.p. >320° C. 1H-NMR (DMSO-d6): 4.86 (s, 1H), 7.29 (m, 3H), 12.24 (s, 1H), 13.28 (br.s, 1H).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-1144d60303fc42d88f7c7d2dfe7821d3
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

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