Hydroxylamine → 2-Fluoro-5-[(hydroxyimino)methyl]benzonitrile

HRID 1250734Notes

Reaction equation

HRID 1250734 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=O)#[N:2].[OH:12][NH2:13].C([O-])(=O)C.[Na+]>C(O)C.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=[N:13][OH:12])#[N:2]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 713582012-Fluoro-5-[(hydroxyimino)methyl]benzonitrileYield 74.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-cyano-4-fluorobenzaldehyde (2.50 g) in ethanol (40 mL) was added a solution of hydroxyamine (1.46 g) in water (10 mL), a solution of sodium acetate (2.75 g) in water (10 mL). The mixture was stirred at rt, overnight. Ethanol was removed and the white precipitate was filtered, washed with water and air dried to leave 3-cyano-4-fluorobenzaldehydeoxime (2.05 g). CI mass spectrum z (rel. intensity) 165 (M+H, 100).

Workup

  1. customEthanol was removed
  2. filtrationthe white precipitate was filtered
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-0e47657081324c5d8a31477717a2e7c6
Source dataset
uspto-grants-2002_01
Patent number
US06339099B1

Reaction notes

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