Water → 4-(6-((3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)pyridazin-3-yloxy)benzoic acid

HRID 215839Notes

Reaction equation

HRID 215839 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[N:12]=[N:13][C:14]([O:17][CH2:18][C:19]3[C:20]([C:27]4[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:34])=[N:21][O:22][C:23]=3[CH:24]([CH3:26])[CH3:25])=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.[OH-].[Na+].O>C(O)C>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=1[C:20]1[C:19]([CH2:18][O:17][C:14]2[N:13]=[N:12][C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:35])=[O:2])=[CH:9][CH:8]=3)=[CH:16][CH:15]=2)=[C:23]([CH:24]([CH3:26])[CH3:25])[O:22][N:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 672970344-{6-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridazin-3-yloxy}-benzoic acid methyl ester

Product 1

HCID 594483194-(6-((3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)pyridazin-3-yloxy)benzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-{6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridazin-3-yloxy}-benzoic acid methyl ester from the previous step (0.083 g, 0.155 mmol) in ethanol (5 ml) was added sodium hydroxide (0.02 g, 0.5 mmol) and water (0.2 ml). The reaction mixture was stirred at room temperature for 20 h. The volatiles were removed in vacuo and the residue was diluted with water (3 ml) and the resulting solution was acidified to pH 5 by addition of 4N HCl. The formed precipitate was collected by filtration, washed with water (3×5 ml) and dried on air to provide 0.08 g (99%) of the title product.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was diluted with water (3 ml)
  3. additionthe resulting solution was acidified to pH 5 by addition of 4N HCl
  4. filtrationThe formed precipitate was collected by filtration
  5. washwashed with water (3×5 ml)
  6. customdried on air

Sources & evidence

ORD record
ord-4e7f2f861cda471ab7351f2c259560ef
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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