Water → HCID 68194160, compound

HRID 1520145Notes

Reaction equation

HRID 1520145 reaction equation
[O:1]=[C:2]1[C:11]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:22]([O:24]C)=[O:23])[CH:8]=2)[NH:3]1.[OH-].[K+].O>CO>[O:1]=[C:2]1[C:11]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:22]([OH:24])=[O:23])[CH:8]=2)[NH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68194205HCID 68194205, compound

Product 1

HCID 68194160HCID 68194160, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-oxo-3-(1,2,3,4-tetrahydroquinolin-1-yl)-1,2-dihydroquinoxaline-6-carboxylate (50 mg, 0.15 mmol) in methanol (30 mL) was added potassium hydroxide (33.33 mg, 0.60 mmol) and water (1 mL) with stifling overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (30 mL), adjusted to pH 4 with HCl (3 N) to give the precipitate, which was collected by filtration to afford 2-oxo-3-(1,2,3,4-tetrahydroquinolin-1-yl)-1,2-dihydroquinoxaline-6-carboxylic acid as a light yellow solid (40.0 mg, 79%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b6388efcec0843df9d82dd12afeaebf4
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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