Hydroxyamine hydrochloride → 2-Chloro-3-fluoro-pyridine-4-carbaldehyde oxime

HRID 1527464Notes

Reaction equation

HRID 1527464 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]=O)[CH:5]=[CH:4][N:3]=1.Cl.[NH2:12][OH:13].C([O-])(=O)C.[NH4+]>CO.O>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]=[N:12][OH:13])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 27631602-Chloro-3-fluoro-4-formylpyridine

Product 1

HCID 1363523242-Chloro-3-fluoro-pyridine-4-carbaldehyde oxime

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-3-fluoro-pyridine-4-carbaldehyde (1.20 g, 5.64 mmol) in MeOH (48 mL) and water (8 mL) were added hydroxylamine hydrochloride (0.59 g, 8.46 mmol) and ammonium acetate (1.30 g, 16.9 mmol), and stirring was continued at RT overnight. The reaction mixture was concentrated in vacuo, and the residue was suspended in CH2Cl2/MeOH 9:1. The precipitate was filtered off, washed with CH2Cl2 and dried to afford the title compound as a white solid. MS (LC/MS): 175.0 [M+H]+; tR (HPLC conditions b): 2.78 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-a4d4d9bdaf8a402aaa9560ba77a6b369
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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