Hydroxyamine hydrochloride → HCID 69672387, compound

HRID 2406395Notes

Reaction equation

HRID 2406395 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12](=[O:18])/[CH:13]=[CH:14]/[N:15](C)C)[CH:2]=[CH2:3].Cl.NO>CO>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12]1[O:18][N:15]=[CH:14][CH:13]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 69672943(2E)-1-[2-(allyloxy)-4-methylphenyl]-3-(dimethylamino)prop-2-en-1-one

Product 1

HCID 69672387HCID 69672387, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of crude (2E)-1-[2-(allyloxy)-4-methylphenyl]-3-(dimethylamino)prop-2-en-1-one (Step 2, 14.1 g, 57.5 mmol) in methanol (70 mL) was added hydroxylamine hydrochloride (4.4 g, 63 mmol) and the reaction was stirred at room temperature for 1 hour. Colourless needle crystals were filtered off and analysed and found to be the title compound, 7.3 g, in a 58% yield. LCMS (2 min acidic) 1.32 min 64-91% pure by UV, ES+/AP+ 216. 1HNMR (400 MHz, CDCl3) δ ppm 2.40 (s, 3H), 4.67 (m, 2H), 5.35 (dq, 1H), 5.46 (dq, 1H), 6.05-6.20 (m, 1H), 6.77 (m, 1H), 6.82 (s, 1H), 6.88-6.92 (m, 1H), 7.88 (d, 1H).

Workup

  1. filtrationColourless needle crystals were filtered off
  2. customLCMS (2 min acidic) 1.32 min 64-91%

Sources & evidence

ORD record
ord-b87444fac372483bbedbba85d97ef755
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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