Sodium Hydroxide → HCID 57520280, compound

HRID 1520168Notes

Reaction equation

HRID 1520168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[C:13]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:14][C:15]3[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([O:24]C)=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6][CH2:5]2.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[C:13]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[N:14][C:15]3[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68194266HCID 68194266, compound

Product 1

HCID 57520280HCID 57520280, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(6-chloro-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (125 mg, 0.28 mmol) in methanol (30 ml) and water (1.0 ml) was added sodium hydroxide (44.6 mg, 1.11 mmol). The reaction was stirred overnight at room temperature. Then the reaction mixture was concentrated in vacuo, dissolved in water (30 ml), adjusted to pH 5 with aqueous hydrochloric acid (3 N) to give a precipitate, which was collected by filtration to afford 3-(6-chloro-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (90 mg, 74%).

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30 ml)
  3. customto give a precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-0c99ef3964c14dfcadd288b108079f12
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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