Sodium Hydroxide → 3-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid

HRID 1405301Notes

Reaction equation

HRID 1405301 reaction equation
[CH3:1][N:2]([CH:27]([CH3:29])[CH3:28])[C:3]1[C:4]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([CH3:26])=[CH:20]3)=[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:27]([CH3:29])[CH3:28])[C:3]1[C:4]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([CH3:26])=[CH:20]3)=[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 70654270methyl 3-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate

Product 1

HCID 706542213-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acidYield 78.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate (660 mg, 1.70 mmol) in methanol (40 ml) was added a solution of NaOH (340 mg, 8.50 mmol) in water (5 ml). The resulting solution was stirred overnight at room temperature and then concentrated in vacuo. The residue was dissolved in water (20 ml), adjusted to pH 4 with HCl (3N). The product was precipitated from water and collected by filtration to afford 3-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid as a orange solid (500 mg, 78%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (20 ml)
  3. customThe product was precipitated from water
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-70deba0206a64ebb985419b7dc23d958
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

Loading…