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

HRID 1063486Notes

Reaction equation

HRID 1063486 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-6fcd434b545c410bad0849bea8e55003
Source dataset
uspto-grants-2005_11
Patent number
US06965036B2

Reaction notes

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