Water → 2-(5-Bromopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid

HRID 1403310Notes

Reaction equation

HRID 1403310 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([O:25]C)=[O:24])[CH:14]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1.[OH-].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([OH:25])=[O:24])[CH:14]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665109Methyl 2-(5-bromopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 509916582-(5-Bromopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(5-bromopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (150.0 mg, 0.36 mmol) in methanol (30 mL) was added sodium hydroxide (43 mg, 1.08 mmol) and water (1 mL) The reaction mixture was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (30 mL) and adjusted to PH 5 with HCl (3 N). The product were collected by filtration to afford 2-(5-bromopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (120.0 mg, 80%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. filtrationThe product were collected by filtration

Sources & evidence

ORD record
ord-21f85bf6f1c943d5b8806b030a62ba15
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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