Sodium Hydroxide → HCID 60198402, compound

HRID 1403347Notes

Reaction equation

HRID 1403347 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:20]([N:21]([CH:23]([CH3:25])[CH3:24])[CH3:22])=[N:19][C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:26]([O:28]C)=[O:27])[CH:17]=4)[N:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O.O1CCCC1>[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:20]([N:21]([CH:23]([CH3:25])[CH3:24])[CH3:22])=[N:19][C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:26]([OH:28])=[O:27])[CH:17]=4)[N:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664668HCID 70664668, compound

Product 1

HCID 60198402HCID 60198402, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(chroman-6-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (130 mg, 0.33 mmol) in water (1 mL) and tetrahydrofuran (5 mL) was added sodium hydroxide (53 mg, 1.33 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (30 mL), adjusted to pH 4 with HCl (3N) to give the precipitate, which was collected by filtration to afford 2-(chroman-6-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (80 mg, 61%).

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-5aaae2f467814a83b549a987cb26635b
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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