Reaction #1256769

Reaction equation

4-Chloro-pyridine-3-carbaldehyde

NaOH

H2O

hydroxylamine hydrochloride

→

4-Chloro-pyridine-3-carbaldehyde Oxime

Solvents

AcOH

EtOH

Conditions

Workup

1. 1
   OtherWhite crystals precipitated
2. 2
   Filtrationwere collected by filtration
3. 3
   Washwashed with H2O (30 ml)
4. 4
   OtherThe product was dried 1 h at 50° C. on the high vacuum
5. 5
   Otherto yield 9.25 g (84%) of a off white solid

Procedure

4-Chloro-pyridine-3-carbaldehyde (10.0 g, 71 mmol) was dissolved in EtOH (12 ml). H2O (30 ml), ice (30 g) and hydroxylamine hydrochloride (5.40 g, 78 mmol) were added. To the resulting mixture was added over a period of 2 min a solution of 2 N NaOH (88.3 ml, 177 mmol). The resulting yellowish solution was stirred 2.5 h at r.t. before neutralisation with AcOH (pH=6). White crystals precipitated, were collected by filtration and washed with H2O (30 ml). The product was dried 1 h at 50° C. on the high vacuum to yield 9.25 g (84%) of a off white solid. m/z=157.1 ([M−H]−).

Source