Sodium Hydroxide → 3-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylic acid

HRID 1403308Notes

Reaction equation

HRID 1403308 reaction equation
[CH:1]([N:4]([CH3:30])[C:5]1[C:6]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH3:29])=[CH:23][CH:22]=3)=[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+]>CO.O>[CH:1]([N:4]([CH3:30])[C:5]1[C:6]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH3:29])=[CH:23][CH:22]=3)=[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 2

HCID 14798Sodium HydroxideHCID 70664737methyl 3-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylate

Product 1

HCID 509916573-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylate (100.0 mg, 0.25 mmol) in methanol (30 mL) was added sodium hydroxide (20.0 mg, 0.50 mmol) in water (1 mL) and stirred overnight at room temperature. The reaction mixture was concentrated under vacuum and dissolved in water (10 mL), adjusted to pH 6 with hydrochloric acid (3N). The solid was precipitated and filtered to afford 3-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylic acid as a light yellow solid as a light yellow solid (23.5 mg, 24%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (10 mL)
  3. customThe solid was precipitated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-40e9dfe3623e4d089fe7084c5fe8c062
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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