O-Methylhydroxylamine hydrochloride → HCID 62553448, compound

HRID 2233424Notes

Reaction equation

HRID 2233424 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=O)=[CH:3][CH:2]=1.Cl.O([NH2:20])C>FC(F)(F)C(O)=O.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([NH2:20])[C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 113562871-(3-Methylphenyl)-2-(pyridin-4-yl)ethan-1-one

Product 1

HCID 62553448HCID 62553448, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

The intermediate oxime was prepared from 2-pyridin-4-yl-1-m-tolyl-ethanone (crude) and methoxylamine hydrochloride (8.00 g, 95.78 mmol) according to the protocol described in general procedure B. The oxime was then dissolved in trifluoroacetic acid (30.00 mL) and Pd/C (0.80 g) was added. The reaction mixture was hydrogenated under 50 psi for 14 hours, then filtered and concentrated. The residue was basified with 5M sodium hydroxide and extracted with methylene chloride. The combined organic phases were dried over potassium carbonate and concentrated to yield the title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 3H) 2.89 (d, J=7.04 Hz, 2 H) 4.12 (t, 1 H) 7.10-7.22 (m, 1 H) 7.39 (ddd, J=7.77, 4.25, 1.47 Hz, 2 H) 7.75-7.82 (m, 1H) 8.41 (td, J=4.98, 2.05 Hz, 2 H) 8.58 (dd, J=5.86, 1.76 Hz, 2 H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic phases were dried over potassium carbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3d700f68197844d594d12233cbba9d89
Source dataset
uspto-grants-2010_05
Patent number
US07709507B2

Reaction notes

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