Sodium Hydroxide → 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid

HRID 1403345Notes

Reaction equation

HRID 1403345 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([C:12]3[C:21]([N:22]([CH:24]([CH3:26])[CH3:25])[CH3:23])=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:27]([O:29]C)=[O:28])[CH:18]=4)[N:13]=3)[CH:10]=[CH:11][C:2]1=2.[OH-].[Na+]>CO.O>[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([C:12]3[C:21]([N:22]([CH:24]([CH3:26])[CH3:25])[CH3:23])=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:27]([OH:29])=[O:28])[CH:18]=4)[N:13]=3)[CH:10]=[CH:11][C:2]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664851methyl 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 601984012-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (140.0 mg, 0.34 mmol) in methanol (30 mL) and water (1 mL) was added sodium hydroxide (42.0 mg, 1.03 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (30 mL) and adjusted to pH 5 with HCl (3N). The solids were collected by filtration to afford 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (120.0 mg, 84%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-a0cf12a573c34fad84aaa71abc1a312a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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