Hydrochloric Acid → 8-Chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carboxylic acid

HRID 240356Notes

Reaction equation

HRID 240356 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:21]([O:23]CC)=[O:22])[C:6](=[O:20])[N:7]2[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:21]([OH:23])=[O:22])[C:6](=[O:20])[N:7]2[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67533339Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl Ester

Product 1

HCID 675332908-Chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carboxylic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.7 g (21.5 mmol) of ethyl 5-chloro-1-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate was dissolved in ethanol (100 ml), and 6.9 g (43.1 mmol) of a 25% aqueous solution of sodium hydroxide was added thereto. The mixture was stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water was added to the residue thus obtained, and the mixture was acidified using 10% hydrochloric acid. A solid precipitated therefrom was separated by filtration, washed with water, and then dried, to obtain 6.7 g (yield: 94%) of 5-chloro-1-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid as a pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. customthus obtained
  4. customA solid precipitated
  5. customtherefrom was separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ebdf7b0fa55f45409467858eff7113dd
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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