Water → 6-Quinoxalinecarboxylic acid, 2-(3-methyl-5-benzofuranyl)-3-[methyl(1-methylethyl)amino]-

HRID 1403490Notes

Reaction equation

HRID 1403490 reaction equation
[CH3:1][N:2]([CH:27]([CH3:29])[CH3:28])[C:3]1[C:4]([C:17]2[CH:18]=[CH:19][C:20]3[O:24][CH:23]=[C:22]([CH3:25])[C:21]=3[CH:26]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=2.[OH-].[Na+].O>CO.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH:27]([CH3:29])[CH3:28])[C:3]1[C:4]([C:17]2[CH:18]=[CH:19][C:20]3[O:24][CH:23]=[C:22]([CH3:25])[C:21]=3[CH:26]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664711HCID 70664711, compound

Product 1

HCID 706653266-Quinoxalinecarboxylic acid, 2-(3-methyl-5-benzofuranyl)-3-[methyl(1-methylethyl)amino]-Yield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 3-[methyl(propan-2-yl)amino]-2-(3-methyl-1-benzofuran-5-yl)quinoxaline-6-carboxylate (110 mg, 0.28 mmol) in methanol (25 mL) and chloroform (5 mL) was added sodium hydroxide (468 mg, 1.17 mmol) and water (2 mL) with stirring for 3 h at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (15 mL), and adjusted pH to 5 with HCl (3N) to give the precipitate, which was collected by filtration to afford 3-[methyl(propan-2-yl)amino]-2-(3-methyl-1-benzofuran-5-yl)quinoxaline-6-carboxylic acid (62 mg, 59%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (15 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3f62704c08af4d22826fcb2950b41064
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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