Sodium Hydroxide → HCID 70665042, compound

HRID 1403598Notes

Reaction equation

HRID 1403598 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH3:22])[CH:19]([CH3:21])[CH3:20])=[N:16][C:15]3[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([C:23]([O:25]C)=[O:24])[CH:14]=3)[N:9]=2)=[CH:4][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]([CH3:22])[CH:19]([CH3:21])[CH3:20])=[N:16][C:15]3[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([C:23]([OH:25])=[O:24])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664867HCID 70664867, compound

Product 1

HCID 70665042HCID 70665042, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-7-methoxy-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (120 mg, 0.31 mmol) in methanol (30 mL) and water (1.0 mL) was added sodium hydroxide (50 mg, 1.25 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 hydrochloric acid (3N) to give the precipitate, which was collected by filtration to afford 2-(4-fluorophenyl)-7-methoxy-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid as a light yellow solid (38.2 mg, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-af2ec4c4565547f6bb6f9ae26f29f014
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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