O-methylhydroxylammonium chloride → HCID 131718641, compound

HRID 1742197Notes

Reaction equation

HRID 1742197 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([F:29])[C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH3:18])[C:10](=[O:17])[C:11]([CH3:16])([C:13](=O)[CH3:14])[O:12][C:7]=2[CH:6]=1.[CH3:30][O:31][NH3+:32].[Cl-]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:21]([F:29])[C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH3:18])[C:10](=[O:17])[C:11]([CH3:16])([C:13](=[N:32][O:31][CH3:30])[CH3:14])[O:12][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 19008597HCID 19008597, compound2×

Product 1

HCID 131718641HCID 131718641, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-(2-Chloro-6-fluoro-4-trifluoromethylphenoxy)-2,4-dimethyl-2-acetyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine (Compound 93) (0.3 g) obtained in Example 15 was dissolved in pyridine (4 ml), o-methylhydroxylamine hydrochloride (0.1 g) was added, and the mixture was stirred at room temperature for 4 hours, and further, at 60° C. for one hour. The reaction mixture was then poured into ice-water, and the mixture was extracted twice with ethyl acetate (20 ml). The extract was washed with 1N-hydrochloric acid and then with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was evaporated under a reduced pressure, and the residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=4/1) to give 0.3 g of the title compound (colorless oil).

Workup

  1. waitfurther, at 60° C. for one hour
  2. extractionthe mixture was extracted twice with ethyl acetate (20 ml)
  3. washThe extract was washed with 1N-hydrochloric acid
  4. dry with materialwith saturated aqueous sodium chloride, and dried over magnesium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-34c9789499e84020942c2bd0f5da6b5b
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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