O-Methylhydroxylamine hydrochloride → HCID 87105951, compound

HRID 1803762Notes

Reaction equation

HRID 1803762 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[C:5]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[CH2:16][CH2:15][C:14]2=O)([CH3:8])([CH3:7])[CH3:6]>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:14]1[C:13]2[C:18](=[C:9]([C:5]([CH3:7])([CH3:6])[CH3:8])[CH:10]=[CH:11][CH:12]=2)[N:17]([CH3:19])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 66684615HCID 66684615, compound

Product 1

HCID 87105951HCID 87105951, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride (0.86 g, 10.3 mmol) was added to a solution of Example 14D (2.04 g, 9.39 mmol) in pyridine (20 mL) and the mixture stirred overnight at ambient temperature. The mixture was concentrated under reduced pressure and ethyl acetate (200 mL) was added. The solution was washed twice with water (200 mL), once with brine, dried over anhydrous sodium sulfate, filtered, and concentrate under reduced pressure. The residue was chromatographed on silica gel eluting with 0-to-25% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.41 (s, 9H), 2.46 (s, 3H), 2.80 (m, 2H), 3.07 (m, 2H), 3.93 (s, 3H), 7.11 (t, J=7.80 Hz, 1H), 7.35 (dd, J=7.97, 1.53 Hz, 1H), 7.62 (dd, J=7.63, 1.53 Hz, 1H). MS (DCI) m/z 247.14 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate (200 mL)
  2. additionwas added
  3. washThe solution was washed twice with water (200 mL), once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrate under reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 0-to-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-35819e1af2134bc5b76bde05fb2430f2
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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