Lithium Hydroxide → 1-Methyl-6-oxo-5-(5-phenyl-4,5-dihydroisoxazol-3-yl)-1,6-dihydropyridazine-3-carboxylic acid

HRID 572690Notes

Reaction equation

HRID 572690 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:10]=2)=[CH:5][C:4]([C:20]([O:22]C)=[O:21])=[N:3]1.[OH-].[Li+]>CO.C1COCC1.O>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:10]=2)=[CH:5][C:4]([C:20]([OH:22])=[O:21])=[N:3]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86675939Methyl 1-methyl-6-oxo-5-(5-phenyl-4,5-dihydroisoxazol-3-yl)-1,6-dihydropyridazine-3-carboxylate

Product 1

HCID 866759381-Methyl-6-oxo-5-(5-phenyl-4,5-dihydroisoxazol-3-yl)-1,6-dihydropyridazine-3-carboxylic acidYield 79%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-methyl-6-oxo-5-(5-phenyl-4,5-dihydroisoxazol-3-yl)-1,6-dihydropyridazine-3-carboxylate (200 mg, 0.638 mmol, Preparation #33) in a mixture of methanol (2 mL) and THF (4 mL) was added lithium hydroxide (30.6 mg, 1.277 mmol, Spectrochem) dissolved in water (2 mL). The reaction mixture was stirred at RT for about 3 h. The reaction mixture was concentrated under vacuum and dissolved in water (10 mL). Further it was acidified to pH 2 with 2N HCl and the solids obtained were collected by filtration to afford 1-methyl-6-oxo-5-(5-phenyl-4,5-dihydroisoxazol-3-yl)-1,6-dihydropyridazine-3-carboxylic acid 0.150 g (79%) as light brown solids. 1H NMR (400 MHz, DMSO) δ 13.8 (br s, 1H), 8.122 (s, 1H), 7.405-7.331 (m, 5H), 5.806-5.757 (m, 1H), 3.958-3.886 (m, 1H) 3.762 (s, 3H), 3.506-3.441 (m, 1H). MS m/z: 298.0 (M−H)−

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (10 mL)
  3. customthe solids obtained
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-875d52d029364f18b1a83001893928f8
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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