Water → HCID 137231113, compound

HRID 2174567Notes

Reaction equation

HRID 2174567 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:19])=[C:7]([C:13]3[O:17][N:16]=[C:15]([CH3:18])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1.[OH-].[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34].O>CO>[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O-:19])=[C:7]([C:13]3[O:17][N:16]=[C:15]([CH3:18])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:27])[CH3:28])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31255Choline, hydroxideHCID 136183528HCID 136183528, compound

Product 1

HCID 137231113HCID 137231113, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7-chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(3-methylisoxazol-5-yl) quinolin-2(1H)-one (Example 42) (1.5 g, 3.79 mmol) in methanol (8 mL) was added choline hydroxide 46% wt in water (1.997 g, 7.58 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, washed with methanol and dried. The resulting solid was recrystallized with acetonitrile to give the title compound 7-chloro-6-(4-(dimethylamino)phenyl)-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate, N-2-hydroxyethyl-N,N-dimethylmethanaminium salt (1.2 g, 2.40 mmol, 63.5% yield) as off-white solid. LCMS: (M+H)+=396; Rt=2.39 min. HRMS: calculated for C21H19ClN3O3 (M+H)+: 396.1115. found: 396.1092.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. customdried
  4. customThe resulting solid was recrystallized with acetonitrile

Sources & evidence

ORD record
ord-71a6b0fa65ae4bb2b29fdae05a0e322f
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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