O-Methylhydroxylamine hydrochloride → HCID 87105706, compound

HRID 1662149Notes

Reaction equation

HRID 1662149 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[CH2:5]([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=O)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 201427181-benzyl-1,2,3,4-tetrahydroquinolin-4-one

Product 1

HCID 87105706HCID 87105706, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride (0.74 g, 8.9 mmol) was added to a solution of Example 15C (1.92 g, 8.1 mmol) in pyridine (20 mL) and stirred overnight at ambient temperature. The mixture was concentrate under reduced pressure, ethyl acetate (200 mL) was added, and the organic layer was washed twice with water (200 mL) and brine, dried over sodium sulfate, filtered, and concentrate under reduced pressure. The residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 2.88 (t, J=6.44 Hz, 2H), 3.29 (t, J=6.44 Hz, 2H), 3.97 (s, 3H), 4.47 (s, 2H), 6.65 (d, J=8.14 Hz, 1H), 6.70 (t, J=7.46 Hz, 1H), 7.13 (td, J=7.80, 1.70 Hz, 1H), 7.31 (m, 5H), 7.92 (dd, J=7.80, 1.70 Hz, 1H). MS (DCI) m/z 267.11 (M+H)+.

Workup

  1. concentrationThe mixture was concentrate under reduced pressure, ethyl acetate (200 mL)
  2. additionwas added
  3. washthe organic layer was washed twice with water (200 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrate under reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-77d251677c354ada95485ffafc108cdc
Source dataset
uspto-grants-2011_10
Patent number
US08030504B2

Reaction notes

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