Sodium Hydroxide → HCID 72488567, compound

HRID 2423488Notes

Reaction equation

HRID 2423488 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[CH:5]=[CH:4][N:3]=1.Cl.[NH2:12][OH:13].[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[C:7]([CH:8]=[N:12][OH:13])=[C:6]([Cl:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 150539852,4-Dichloropyridine-3-carbaldehyde

Product 1

HCID 72488567HCID 72488567, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 2,4-dichloro-3-pyridinecarbaldehyde (2.15 g, 12.4 mmol) in ethanol (18 mL) was added to a solution of hydroxylamine hydrochloride (1.01 g, 14.5 mmol) and sodium hydroxide (0.58 g, 14.5 mL) in water (9 mL). The resulting solution was heated in a 65° C. oil bath for 3 hours. The mixture was filtered to yield a white solid which was dried in a vacuum oven at 45° C. with P2O5 to yield 2,4-dichloro-3-pyridinecarbaldehyde oxime (1.89 g, 80%). 1H NMR (400 MHz, DMSO-d6): δ 12.00 (s, 1H), 8.35 (d, J=5 Hz, 1H), 8.19 (s, 1H), 7.68 (d, J=5 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customto yield a white solid which
  3. dry with materialwas dried in a vacuum oven at 45° C. with P2O5

Sources & evidence

ORD record
ord-e07fdaa7a6964ae2bf215fa2a65af8c1
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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