Acetic Acid → HCID 57520279, compound

HRID 1520165Notes

Reaction equation

HRID 1520165 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[C:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:15][C:16]3[C:21]([N:22]=1)=[CH:20][C:19]([C:23]([O:25]C)=[O:24])=[CH:18][CH:17]=3)[CH2:8][CH2:7][CH2:6]2.[OH-].[Na+].CC(O)=O>CO.O>[CH3:1][N:2]([CH3:34])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[C:14]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[N:15][C:16]3[C:21]([N:22]=1)=[CH:20][C:19]([C:23]([OH:25])=[O:24])=[CH:18][CH:17]=3)[CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 68194056HCID 68194056, compound

Product 1

HCID 57520279HCID 57520279, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 3-[6-(dimethylamino)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylate (30 mg, 0.07 mmol) in methanol (20 ml) and water (2 ml) was added sodium hydroxide (10 mg, 0.25 mmol) and the reaction was stirred overnight at room temperature. The resulting solution was diluted with water (100 ml), adjusted pH to 5 with AcOH, extracted with ethyl acetate (3×20 ml), dried over anhydrous magnesium sulfate and concentrated in vacuo to give 3-[6-(dimethylamino)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a red solid (3 mg, 10%).

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98d7f8a23d4b45b8b6124292cfb81f9d
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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