Hydroxyamine hydrochloride → HCID 136350288, compound

HRID 1506301Notes

Reaction equation

HRID 1506301 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([CH:16]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>C(O)C>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([CH:16]=[N:19][OH:20])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 72213375HCID 72213375, compound

Product 1

HCID 136350288HCID 136350288, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbaldehyde (Intermediate I-12B, 0.38 g, 1.576 mmol) in ethanol (5 mL) were sequentially added hydroxylamine hydrochloride (0.131 g, 1.891 mmol) and sodium acetate (0.155 g, 1.891 mmol) at room temperature. The reaction mixture was heated at 80° C. for 20 min. The reaction mixture was concentrated and water (10 ml) was added. A pale yellow solid separated out from solution, and was filtered, washed with water (2×5 mL) and dried overnight to yield 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbaldehyde oxime (0.35 g, 1.366 mmol, 87% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (br. s., 1H) 8.32 (s, 1H) 7.62-7.67 (m, 2H) 7.47-7.57 (m, 3H).

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additionwater (10 ml) was added
  4. customA pale yellow solid separated out from solution
  5. filtrationwas filtered
  6. washwashed with water (2×5 mL)
  7. customdried overnight

Sources & evidence

ORD record
ord-e9ee85fd01ed465997cad51010b598b5
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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