Sodium Hydroxide → HCID 70664747, compound

HRID 1403318Notes

Reaction equation

HRID 1403318 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([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)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>CO.C(Cl)(Cl)Cl.O>[F:1][C:2]1[CH:7]=[C:6]([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)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 70665012HCID 70665012, compound

Product 1

HCID 70664747HCID 70664747, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-(2-fluoropyridin-4-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (125.0 mg, 0.35 mmol) in methanol (25 mL) and chloroform (10 mL) was added sodium hydroxide (56.0 mg, 1.40 mmol) in water (1 mL). The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (20 mL) and adjusted to pH 6 with hydrochloric acid (1N). The product was precipitated and collected by filtration to afford 2-(2-fluoropyridin-4-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a yellow solid (50 mg, 42%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (20 mL)
  3. customThe product was precipitated
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9e29bb0a02db46c584f0cf8ecd0402a1
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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