Hydrochloric Acid → HCID 178524852, compound

HRID 336350Notes

Reaction equation

HRID 336350 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([C:13]([O:15]CC)=[O:14])[C:6]([OH:18])=[N:5]2.O.[OH-].[Li+].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([C:13]([OH:15])=[O:14])[C:6]([OH:18])=[N:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178470162HCID 178470162, compound

Product 1

HCID 178524852HCID 178524852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 6,7-difluoro-3-hydroxyquinoxaline-2-carboxylate (500 mg, 2.0 mmol) and lithium hydroxide monohydrate (330 mg, 7.9 mmol) in THF (10 mL) and water (5 mL) was heated at 50° C. under nitrogen for 1 h. The mixture was further cooled to 0° C., acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (100 mL). The organic extract was washed with brine (50 mL), dried over magnesium sulfate, filtered and the solvents were removed under reduced pressure to provide 6,7-difluoro-3-hydroxyquinoxaline-2-carboxylic acid as a yellow solid: 1H NMR (400 MHz, CD3OD) δ 7.88 (dd, 1H), 7.29 (dd, 1H) ppm; ESI MS m/z 225 [M−H]−.

Workup

  1. temperatureThe mixture was further cooled to 0° C.
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. washwas washed with brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-8d076824c4044512a3f1acaeea8a3de4
Source dataset
uspto-grants-2014_11
Patent number
US08889683B2

Reaction notes

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