Sodium Hydroxide → 3-(4-Methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 716877Notes

Reaction equation

HRID 716877 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=3)[CH2:4][CH2:3]1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=3)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67041699HCID 67041699, compound

Product 1

HCID 509919423-(4-Methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Solutions of methyl 3-(4-methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylate (249.7 mg, 0.55 mmol, 1.00 equiv.) in THF/MeOH (1:1) (20 mL) and sodium hydroxide (138 mg, 3.45 mmol, 5.00 equiv) in water (1.5 mL) were placed in a 50-mL round bottom flask, stirred for 3 hrs at 30° C. in an oil bath, concentrated under vacuum, and washed with DCM. This resulted in 90 mg (45%) of 3-(4-methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with DCM
  3. customThis resulted in 90 mg (45%) of 3-(4-methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-e678d99ccd9f4c58b609b0d13bfcad6e
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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