Hydrochloric Acid → HCID 178525365, compound

HRID 2297523Notes

Reaction equation

HRID 2297523 reaction equation
[OH:1][C:2]1[C:3]([CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CN(C)C=O.[OH-].[Li+].Cl>CS(C)=O.O>[OH:1][C:2]1[C:3]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 6228Dimethylformamide2×HCID 178500070HCID 178500070, compound

Product 1

HCID 178525365HCID 178525365, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Methyl 3-(3-hydroxyquinoxaline-2-yl)propanoate (701 mg) was dissolved in dimethylsulfoxide (8 ml), dimethylformamide (8 ml), dimethylformamide (20 ml) and water (10 ml), and then lithium hydroxide (80 mg) was added to the solution, followed by stirring the mixture overnight at room temperature. Then lithium hydroxide (110 mg) was further added and the mixture was stirred for 2 days. To the reaction solution, 1N hydrochloric acid was added and the resulting mixture was extracted 3 times with ethyl acetate. Organic layers were combined and washed with brine. The resultant was dried over anhydrous sodium sulfate and then concentrated to obtain 642 mg of 3-(3-hydroxyquinoxaline-2-yl)propanoic acid Yield: 97%.

Workup

  1. stirringthe mixture was stirred for 2 days
  2. extractionthe resulting mixture was extracted 3 times with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe resultant was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5feef259e7d4446b988b711319e879a
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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