Lithium hydroxide, monohydrate → 1-[(3-Methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid

HRID 240347Notes

Reaction equation

HRID 240347 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]([O:20]CC)=[O:19])[C:9]2=[O:23])[O:4][N:3]=1.O.[OH-].[Li+]>C(O)C.O>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]([OH:20])=[O:19])[C:9]2=[O:23])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67533297Ethyl 1-[(3-methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

Product 1

HCID 675325101-[(3-Methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acidYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3.0 g (9.58 mmol) of ethyl 1-[(3-methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylate and 0.46 g (11.5 mmol) of lithium hydroxide monohydrate were dissolved in a solvent mixture of ethanol (30 mL) and water (30 mL), and the solution was stirred for 2 hours at room temperature. The reaction solution was concentrated to a half the original volume, and water was added to the residue. The mixture was acidified using 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated, to obtain 2.3 g (yield: 84%) of 1-[(3-methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated to a half the original volume, and water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b040ab6d25b44379ae1c85f94e678bd
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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