Sodium Hydroxide → Sodium 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

HRID 2423391Notes

Reaction equation

HRID 2423391 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[N:28]=[C:27]([C:32]([OH:34])=[O:33])[CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:35]([CH3:37])[CH3:36])[O:11][N:10]=1.[OH-].[Na+:39]>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[N:28]=[C:27]([C:32]([O-:34])=[O:33])[CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:35]([CH3:37])[CH3:36])[O:11][N:10]=1.[Na+:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 247719836-(4-{[3-(2,6-Dichlorophenyl)-5-(1-Methylethyl)isoxazol-4-Yl]methoxy}phenyl)quinoline-2-Carboxylic Acid

Product 1

HCID 67243637Sodium 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylateYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring suspension of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (4.12 g, 7.73 mmol) in methanol (100 mL) was added 1 N sodium hydroxide (7.73 mL, 7.73 mmol). The mixture was stirred for approximately 1 hour and then concentrated. Ether was added followed by a little water. After stirring the solid turned into a paste. The solvent was decanted and the paste triturated with ether and then dried on a rotary evaporator at 35° C. under vacuum for approximately 1.5 hours to afford sodium 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (4.24 g, 98%). 1H-NMR (400 MHz, DMSO-d6) δ 8.28-8.22 (m, 2H), 8.09-7.96 (m, 3H), 7.68 (d, J=9 Hz, 2H), 7.63-7.51 (m, 3H), 6.90 (d, J=9 Hz, 2H), 4.87 (s, 2H), 3.46 (septet, J=7 Hz, 1H), 1.33 (d, J=7 Hz, 6H). LRMS (APCI) C29H21Cl2N2O4Na calculated: 533 (M+H)+, found: 533 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionEther was added
  3. stirringAfter stirring the solid
  4. customThe solvent was decanted
  5. customthe paste triturated with ether
  6. customdried on a rotary evaporator at 35° C. under vacuum for approximately 1.5 hours

Sources & evidence

ORD record
ord-82ca6b18c7a04fe697f71ce87ed84f7a
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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