Sodium Hydroxide → 3-[Methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acid

HRID 1403402Notes

Reaction equation

HRID 1403402 reaction equation
[CH3:1][N:2]([CH:28]([CH3:30])[CH3:29])[C:3]1[C:4]([C:17]2[O:18][CH:19]=[C:20](C3C=CC=CC=3)[CH:21]=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+]>CO.O>[CH3:1][N:2]([CH:28]([CH3:29])[CH3:30])[C:3]1[C:4]([C:17]2[O:18][C:19]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:20][CH:21]=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

5

Reactant 2

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

Product 1

HCID 601985343-[Methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acidYield 172.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[methyl(propan-2-yl)amino]-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylate (50 mg, 0.12 mmol) in methanol (30 mL) and water (2 mL) was added sodium hydroxide (19.9 mg, 0.50 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (30 mL) and adjusted to pH 5 with HCl (3 N). The solids were collected by filtration to afford 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acid as a light yellow solid (40 mg, 83%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-f3be296cf5f84e578b132e4423bab218
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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