Water → 3-(Isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylic acid

HRID 1403472Notes

Reaction equation

HRID 1403472 reaction equation
[CH:1]([N:4]([CH3:30])[C:5]1[C:6]([C:19]2[O:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:23]=2)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[CH:1]([N:4]([CH3:30])[C:5]1[C:6]([C:19]2[O:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:23]=2)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 60171729Methyl 3-(isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylate

Product 1

HCID 706646673-(Isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylic acidYield 65.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylate (70 mg, 0.17 mmol) in MeOH (20 mL) was added sodium hydroxide (28 mg, 0.70 mmol) and water (2 mL). The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (3 mL) and adjusted to pH 6 with HCl (1N). The solids were collected by filtration to afford 3-(isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylic acid (43 mg, 64%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (3 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-612a30fddd7d4854acd4a5dd76be33c9
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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