O-Methylhydroxylamine hydrochloride → HCID 57377783, compound

HRID 1184393Notes

Reaction equation

HRID 1184393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[N:11][CH:12]=[C:13]([CH:24]=2)[C:14]([NH:16][CH2:17][C:18](=O)[C:19]([F:22])([F:21])[F:20])=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:32][O:33][NH2:34]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([O:25][CH2:26][C:27]([F:30])([F:28])[F:29])=[N:11][CH:12]=[C:13]([CH:24]=2)[C:14]([NH:16][CH2:17]/[C:18](=[N:34]/[O:33][CH3:32])/[C:19]([F:20])([F:21])[F:22])=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86667097HCID 86667097, compound

Product 1

HCID 57377783HCID 57377783, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.241 g 5-(3,4-dichloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-N-(3,3,3-trifluoro-2-oxo-propyl)-nicotinamide in ethanol was added 0.051 g O-methylhydroxylamine hydrochloride and the mixture was kept at ambient temperature for 18 h. The mixture was then heated to reflux for 4 h. The clear reaction mixture was diluted with ca 2 ml water and concentrated under aspirator vacuum whereby crystallisation occurred. The product was collected by filtration and washed with water and dried to constant weight under high vacuum to yield 0.23 g of the title compound as white crystals melting at 124-126° C. MS (EI): 502.1 (M−H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated under aspirator vacuum whereby crystallisation
  4. filtrationThe product was collected by filtration
  5. washwashed with water
  6. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-c263723f447b442a815c91d972fd1923
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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