Sodium Hydroxide → HCID 70664749, compound

HRID 1403579Notes

Reaction equation

HRID 1403579 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([O:25]C)=[O:24])[CH:14]=3)[N:9]=2)=[C:4]([CH3:27])[CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([OH:25])=[O:24])[CH:14]=3)[N:9]=2)=[C:4]([CH3:27])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664633HCID 70664633, compound

Product 1

HCID 70664749HCID 70664749, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-fluoro-2-methylphenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (45 mg, 0.12 mmol) in methanol (35 mL) and water (2.0 mL) was added sodium hydroxide (20 mg, 0.50 mmol) and the reaction was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (20 mL) and adjusted to pH 4 with aqueous HCl (3N). The solids were collected by filtration to afford 2-(4-fluoro-2-methylphenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (36 mg, 83%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (20 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-2df156b8bcb34be4a5e0cf5a9d145a28
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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