Sodium Hydroxide → HCID 70664929, compound

HRID 1403564Notes

Reaction equation

HRID 1403564 reaction equation
[C:1]([NH:5][C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.O>[C:1]([NH:5][C:6]1[C:7]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664982HCID 70664982, compound

Product 1

HCID 70664929HCID 70664929, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(tert-butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (120 mg, 0.34 mmol) in THF (20 mL) and water (2 mL) was added sodium hydroxide (54.39 mg, 1.36 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (30 mL), adjusted to pH 4 with HCl (3N) to give the precipitate, which was collected by filtration to afford 3-(tert-butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (80 mg, 66%).

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-a6fe8f79a2eb49dfb8750590f9a3d7cd
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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