Sodium Hydroxide → HCID 137190312, compound

HRID 929757Notes

Reaction equation

HRID 929757 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]=O)=[N:10][CH:11]=1.CCO.[OH2:21].Cl.[NH2:23]O.[OH-].[Na+]>CC(O)=O>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]=[N:23][OH:21])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19096565Water ethanol2×HCID 79794746HCID 79794746, compound2×

Product 1

HCID 137190312HCID 137190312, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-(2-Chloro-benzyloxy)-pyridine-2-carbaldehyde (which may be prepared as described in Preparation of Intermediate 7; 2.06 g, 8.3 mmol) was suspended in 9:1 EtOH/H2O (20 mL) and hydroxylamine hydrochloride (1.45 g, 20.9 mmol) was added. A solution of 3.25 M NaOH in 9:1 EtOH/H2O (6.5 mL, 21.1 mmol) was added slowly dropwise. The mixture was heated under reflux for 2.5 h and then cooled to 0° C. The pH was adjusted to 4 by the addition of glacial AcOH. The precipitate was filtered off to give 5-(2-chloro-benzyloxy)-pyridine-2-carbaldehyde oxime (1.5 g, 69%) as an off-white solid.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2.5 h
  4. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-f1a935d190d7472d8019743d27546e9a
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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