Sodium Hydroxide → HCID 57520108, compound

HRID 1520142Notes

Reaction equation

HRID 1520142 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]4[C:29]5[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=5)[CH2:23][CH2:22][CH2:21]4)=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:32]([O:34]C)=[O:33])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:36]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]4[C:29]5[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=5)[CH2:23][CH2:22][CH2:21]4)=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:32]([OH:34])=[O:33])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:36]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68194261HCID 68194261, compound

Product 1

HCID 57520108HCID 57520108, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(5-fluoro-1-benzofuran-2-yl)-3-(6-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (40 mg, 0.083 mmol) in methanol (20 mL) and water (three drops) was added sodium hydroxide (16.5 mg, 0.41 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (30 mL), adjusted to pH 5 with hydrogen chloride (3 N) to give the precipitation, which was collected by filtration to afford 2-(5-fluoro-1-benzofuran-2-yl)-3-(6-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylic acid as a light yellow solid (23 mg, 44%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 mL)
  3. customto give
  4. customthe precipitation, which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3cdddcc3038b436597b356b36576b767
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

Loading…