Hydroxyamine hydrochloride → 2-Fluoro-3-methoxybenzaldehyde oxime

HRID 400543Notes

Reaction equation

HRID 400543 reaction equation
C(=O)([O-])O.[Na+].Cl.[NH2:7][OH:8].[F:9][C:10]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O>O.C(O)C>[F:9][C:10]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[N:7][OH:8]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 37744632-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 762208362-Fluoro-3-methoxybenzaldehyde oximeYield 85.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of sodium hydrogen carbonate (2.73 g, 32.5 mmol) in water (50 mL) was added hydroxylamine hydrochloride (2.30 g, 33.2 mmol) in portions over 30 min. The resultant solution was added to a vigorously stirred suspension of 2-fluoro-3-methoxybenzaldehyde (5.00 g, 32.5 mmol) in ethanol (45 mL) and the reaction mixture stirred at RT for 16 hr. The resultant precipitate was removed by filtration and washed with water (3×100 mL) and then allowed to dry in air to afford 2-fluoro-3-methoxybenzaldehyde oxime (14) (4.69 g, 85%) as a white crystalline solid: m/z 170 (M+H)+ (ES+).

Workup

  1. customThe resultant precipitate was removed by filtration
  2. washwashed with water (3×100 mL)
  3. customto dry in air

Sources & evidence

ORD record
ord-e13b98602b3d4808ae9f22c157aa7c25
Source dataset
uspto-grants-2014_06
Patent number
US08741909B2

Reaction notes

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