Acetic Acid → N-[(2,5-Difluorophenyl)methylidene]hydroxylamine

HRID 2265912Notes

Reaction equation

HRID 2265912 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:12][OH:13].[OH-].[Na+].C(O)(=O)C>CCO.O>[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[N:12][OH:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 1376632,5-DifluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 57371077N-[(2,5-Difluorophenyl)methylidene]hydroxylamineYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2,5-Difluorobenzaldehyde (28.5 g, 0.20 mol) was dissolved in 30 ml EtOH. 80 ml water, 80 g crushed ice and hydroxylamine hydrochloride (15.3 g, 0.22 mol) were added. 250 ml (0.50 mol) 2N NaOH were added drop wise and the yellow solution was stirred for 3 hours at room temperature. The reaction mixture was neutralized to pH 6 with acetic acid. The formed suspension was diluted with water and filtered. The crystals were washed with water and dried 2 hours at 50° C. and <20 mbar to obtain the desired product as a white solid (26.1 g, 83%). MS (m/e): 156.0 (M−H+).

Workup

  1. additionwere added
  2. filtrationfiltered
  3. washThe crystals were washed with water
  4. customdried 2 hours at 50° C.

Sources & evidence

ORD record
ord-cf8be64000aa424bb5ae7f2eb474068b
Source dataset
uspto-grants-2010_12
Patent number
US07858630B2

Reaction notes

Loading…