O-Methylhydroxylamine hydrochloride → HCID 87105537, compound

HRID 1803751Notes

Reaction equation

HRID 1803751 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][C:12](=O)[CH2:13][O:14]2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:12]1[CH2:11][C:10]2[C:15](=[CH:16][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)[O:14][CH2:13]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 117690977-methoxychroman-3-one

Product 1

HCID 87105537HCID 87105537, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxyl amine hydrochloride (459 mg, 5.49 mmol) was added to a solution of Example 3C (890 mg, 4.99 mmol) in pyridine (20 mL) and the mixture was stirred overnight at ambient temperature. The mixture was concentrated under reduced pressure, taken up in ethyl acetate (100 mL) and 1N hydrochloric acid (100 mL). The separated organic layer was washed with brine, filtered, and dried over anhydrous sodium sulfate. Concentration and chromatography on silica gel eluting with 0-to-20% ethyl acetate in hexane afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.64 (s, 2H), 3.70 (s, 3H), 3.85 (s, 3H), 4.49 (s, 2H), 6.47 (d, J=2.72 Hz, 1H), 6.57 (dd, J=8.48, 2.38 Hz, 1H), 7.10 (d, J=8.48 Hz, 1H). MS (DCI) m/z 208.05 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washThe separated organic layer was washed with brine
  3. filtrationfiltered
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration and chromatography on silica gel eluting with 0-to-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-72c02389fcbe4b62a1ee3c7408a82bf0
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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