Sodium Hydroxide → HCID 57520109, compound

HRID 1520144Notes

Reaction equation

HRID 1520144 reaction equation
[Cl: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]([F:30])=[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:31]([O:33]C)=[O:32])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:35]=1.[OH-].[Na+]>CO.O>[Cl: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]([F:30])=[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:31]([OH:33])=[O:32])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:35]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68194228HCID 68194228, compound

Product 1

HCID 57520109HCID 57520109, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(5-chloro-1-benzofuran-2-yl)-3-(6-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (53 mg, 0.11 mmol) in methanol (25 mL) and water (1 mL) was added sodium hydroxide (12.0 mg, 0.30 mmol) with stifling overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (10 mL), adjusted pH to 5 with hydrogen chloride (3 N) to give the precipitation, which was collected by filtration to afford 2-(5-chloro-1-benzofuran-2-yl)-3-(6-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylic acid (37.5 mg, 73%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (10 mL)
  3. customto give
  4. customthe precipitation, which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-72f412a91447426e8fb308cfdfeefa34
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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