Sodium Hydroxide → HCID 70665140, compound

HRID 1403478Notes

Reaction equation

HRID 1403478 reaction equation
[CH3:1][N:2]([CH:22]([CH3:24])[CH3:23])[C:3]1[C:4]([C:17]2[CH:21]=[CH:20][NH:19][CH:18]=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>[CH3:1][N:2]([CH:22]([CH3:24])[CH3:23])[C:3]1[C:4]([C:17]2[CH:21]=[CH:20][NH:19][CH:18]=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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70664629HCID 70664629, compound

Product 1

HCID 70665140HCID 70665140, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[methyl(propan-2-yl)amino]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylate (70 mg, 0.22 mmol) in methanol (40 mL) was added NaOH (34.6 mg, 0.87 mmol) with stirring for 2 h at room temperature. The resulting mixture was concentrated under vacuum and extracted with dichloromethane (20 mL). The aqueous layers were combined, adjusted to pH 6 with HCl (3 N), and the product was collected by filtration to give 3-[methyl(propan-2-yl)amino]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylic acid as a yellow solid (18.6 mg, 28%).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. extractionextracted with dichloromethane (20 mL)
  3. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-c0fd3aaf2d9147d98b048479aad9cceb
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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