Hydroxyamine hydrochloride → HCID 68276004, compound

HRID 1626044Notes

Reaction equation

HRID 1626044 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([CH:10]([C:15](=O)[CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:21]O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:16][C:15]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([C:7]2[CH:18]=[CH:19][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[O:9][N:21]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 539799HCID 539799, compound

Product 1

HCID 68276004HCID 68276004, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

Methyl 2-(4-nitrobenzoyl)-3-oxobutanoate (20.0 g, 75.47 mmol) was dissolved in acetic acid (70 mL), and followed by adding hydroxylamine hydrochloride (5.10 g, 73.27 mmol). The reaction was stirred at 115° C. for 2 hours. After cooling the reaction to the RT, 400 mL saturated NaHCO3 was added into the solution and extracted by ethyl acetate for 3 times. The combined organic layer was washed by brine and dried over Na2SO4, and removed under the vacuum. The crude product was further purified by flash chromatography using EA/Hexane=1:9 to give methyl 3-methyl-5-(4-nitrophenyl)isoxazole-4-carboxylate (16.4 g, 83% yield). MS m/z 263.1 (M+1).

Workup

  1. temperatureAfter cooling
  2. additionwas added into the solution
  3. extractionextracted by ethyl acetate for 3 times
  4. washThe combined organic layer was washed by brine
  5. dry with materialdried over Na2SO4
  6. customremoved under the vacuum
  7. customThe crude product was further purified by flash chromatography

Sources & evidence

ORD record
ord-b1238f3f1d504266aa0612071f6a52ac
Source dataset
uspto-grants-2014_07
Patent number
US08785442B2

Reaction notes

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