Hydroxyamine hydrochloride → 3-Fluoro-2-trifluoromethyl-pyridine-4-carbaldehyde oxime

HRID 1527468Notes

Reaction equation

HRID 1527468 reaction equation
[F:1][C:2]1[C:3]([C:10]([F:13])([F:12])[F:11])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=O.Cl.[NH2:15][OH:16].C([O-])(=O)C.[NH4+]>CO.O>[F:1][C:2]1[C:3]([C:10]([F:13])([F:12])[F:11])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[N:15][OH:16]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 866738643-Fluoro-2-(trifluoromethyl)pyridine-4-carbaldehyde

Product 1

HCID 1363523253-Fluoro-2-trifluoromethyl-pyridine-4-carbaldehyde oxime

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-fluoro-2-trifluoromethyl-pyridine-4-carbaldehyde (0.495 g, 2.05 mmol) in MeOH (17.6 mL) and water (2.9 mL) were added hydroxylamine hydrochloride (0.214 g, 3.08 mmol) and ammonium acetate (0.474 g, 6.15 mmol), and the resulting mixture was stirred at RT overnight. Volatile were removed 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): 209.0 [M+H]+; tR (HPLC conditions c): 4.28 min.

Workup

  1. customVolatile were removed in vacuo
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-423f296eef0f41c09ce34e77d16bcefb
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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