Sodium Hydroxide → 4-(2-Pyridyl)-benzaldehyde oxime

HRID 2041169Notes

Reaction equation

HRID 2041169 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1>O.C(O)C>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[N:2][OH:3])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 15152404-Pyridin-2-ylbenzaldehyde

Product 1

HCID 1364150684-(2-Pyridyl)-benzaldehyde oximeYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Add hydroxylamine hydrochloride (0.379 g, 5.458 mmol) and a solution of NaOH (0.327 g, 8.187 mmol) in water (2 mL) to a solution of 4-(2-pyridyl)-benzaldehyde (0.5 g, 2.729 mmol) in ethanol (10 mL). Heat the mixture at 80° C. for 2 h. Cool to ambient temperature and remove the solvent in vacuo. Partition the residue between EtOAc and water. Separate and day the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1) to obtain the desired intermediate (311 mg, 58%). GC-MS m/z: 198 (M+).

Workup

  1. temperatureCool to ambient temperature
  2. customremove the solvent in vacuo
  3. customPartition the residue between EtOAc and water
  4. customSeparate and day the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1)

Sources & evidence

ORD record
ord-ec5007b5249b4631b92cd0fd782f3637
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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