Sodium Hydroxide → HCID 72255374, compound

HRID 2423493Notes

Reaction equation

HRID 2423493 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[CH3:6][C:7]1[C:12]([CH:13]=O)=[C:11]([CH3:15])[CH:10]=[CH:9][N:8]=1>O.C(O)C>[CH3:6][C:7]1[C:12]([CH:13]=[N:2][OH:3])=[C:11]([CH3:15])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 104417552,4-Dimethylnicotinaldehyde

Product 1

HCID 72255374HCID 72255374, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of hydroxylamine hydrochloride (0.21 g, 3.0 mmol) and sodium hydroxide (0.12 g, 3.0 mmol) in water (1.9 mL) was added to a solution of 2,4-dimethyl-3-pyridinecarbaldehyde (0.35 g, 2.6 mmol) in ethanol (3.8 mL). The solution was heated in a 65° C. oil bath for 2 hours. The mixture was concentrated and the residue diluted with water and filtered. The resulting white solid was dried in a 45° C. vacuum oven with P2O5 to yield 2,4-dimethyl-3-pyridinecarbaldehyde oxime (345 mg, 88%). 1H NMR (400 MHz, DMSO-d6): δ 11.44 (s, 1H), 8.33 (s, 1H), 8.23 (d, J=5 Hz, 1H), 7.08 (d, J=5 Hz, 1H), 2.48 (s, overlapping DMSO), 2.33 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue diluted with water
  3. filtrationfiltered
  4. dry with materialThe resulting white solid was dried in a 45° C. vacuum oven with P2O5

Sources & evidence

ORD record
ord-ad852091917c4b0cb112d7846cfad177
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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