Hydrochloric Acid → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

HRID 1958076Notes

Reaction equation

HRID 1958076 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[C:15]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:16][O:17][C:18]=2[CH3:19])=[CH:10][CH:11]=1)=[O:5])C.O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:20]([C:15]1[C:14]([CH2:13][O:12][C:9]2[N:8]=[N:7][C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=2)=[C:18]([CH3:19])[O:17][N:16]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 666439586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

Product 1

HCID 666440146-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester (960 mg, 3.0 mmol) in THF (10 mL) was added a solution of lithium hydroxide monohydrate (252 mg, 6.0 mmol) in water (10 mL) and the resulting mixture stirred at room temperature for 30 min. The mixture was acidified to pH 1 with HCl (1 N) and the resulting mixture extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title compound (850 mg, 87%) which was obtained as a red gum. MS: m/e=290.1 [M−H]−.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d4e00ac7b0a94cc1a8d7d580131ca769
Source dataset
uspto-grants-2013_04
Patent number
US08410104B2

Reaction notes

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