Sodium Hydroxide → HCID 70664752, compound

HRID 1403642Notes

Reaction equation

HRID 1403642 reaction equation
[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[C:5]1[C:6]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[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)[CH2:2][CH3:3].[OH-].[Na+]>CO.O>[CH2:26]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[C:6]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)=[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)[CH2:27][CH3:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664992HCID 70664992, compound

Product 1

HCID 70664752HCID 70664752, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(dipropylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (50 mg, 0.13 mmol) in methanol (15 mL) was added a solution of sodium hydroxide (10 mg, 0.25 mmol) in water (1 mL). The resulting solution was stirred overnight at room temperature and then concentrated in vacuo. The residue was dissolved in water (20 mL) and adjusted to pH 5 with hydrochloric acid (3N). The resulting solution was extracted with dichloromethane (4×20 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 3-(dipropylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a yellow solid (22.4 mg, 46%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (20 mL)
  3. extractionThe resulting solution was extracted with dichloromethane (4×20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff10e4bc70c14726bd4b6311042ca5c3
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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