Methanol → 1-(Pyridin-4-yl)propan-1-one oxime

HRID 371399Notes

Reaction equation

HRID 371399 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(=O)[CH2:5][CH3:6].CO>O.[OH-].[Na+]>[C:4](=[N:2][OH:3])([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 743431-(4-Pyridinyl)-1-propanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1363417421-(Pyridin-4-yl)propan-1-one oximeYield 75.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of hydroxylamine hydrochloride (7 g, 0.1 mol) in H2O (40 mL) and 2N NaOH solution (50 mL) was added the compound 1 (9.46 g, 70 mmol). The reaction mixture was heated to reflux and made homogeneous by the addition of methanol (MeOH) (30 mL). After heating at reflux for 2 hours, the reaction mixture upon cooling gave the compound 2 as a white solid (7.90 g, 75%): mp 141°-144° C.; NMR (DMSO-d6) δ 1.03 (t, 3H, J=8 Hz), 2.72 (q, 2H, J=8 Hz), 3.34 (bs, 1H), 7.56 (d of d, 2H), and 8.56 (df d, 2H); IR (KBr) 1600 cm-1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureAfter heating
  4. temperatureat reflux for 2 hours
  5. temperaturethe reaction mixture upon cooling

Sources & evidence

ORD record
ord-8685ceb6c41c4706ab39850dce305d87
Source dataset
uspto-grants-1985_07
Patent number
US04532250

Reaction notes

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