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

HRID 968352Notes

Reaction equation

HRID 968352 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].Cl.[OH:13][NH2:14]>C(O)C.N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=[N:14][OH:13])#[N:2]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 713582012-Fluoro-5-[(hydroxyimino)methyl]benzonitrileYield 91.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

3-Cyano-4-fluorobenzaldehyde (5.00 g) and hydroxyamine hydrochloride (2.90 g, 1.25 Eq) were dissolved in ethanol (100 mL) and pyridine (100 mL). The mixture was stirred at RT under N2 for 45 minutes. The solvents were removed and the brown oil was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated to give 3-cyano-4-fluorobenzaldehydeoxime (5.03 g). CI mass spectrum z (rel. intensity) 165 (M+H, 100).

Workup

  1. customThe solvents were removed
  2. customthe brown oil was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9212869856c04dac9e2c4ac5725dd779
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

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