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

HRID 1071467Notes

Reaction equation

HRID 1071467 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-3e4b34aac94f4e99b7b8efb2458453b3
Source dataset
uspto-grants-2005_06
Patent number
US06906070B2

Reaction notes

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