Sodium Carbonate → N-[(4-fluorophenyl)methylidene]hydroxylamine

HRID 2406485Notes

Reaction equation

HRID 2406485 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][OH:11].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:10][OH:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 680234-FluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 68017N-[(4-fluorophenyl)methylidene]hydroxylamineYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-fluorobenzaldehyde (3.0 g, 24.1 mmol) in MeOH (15 mL) was added NH2OH.HCl (2.0 g, 29.1 mmol) and Na2CO3 (1.53 g, 14.4 mmol) and the reaction stirred for 4 hours at room temperature. The reaction was concentrated under reduced pressure, extracted with DCM (2×100 mL), and the organic layer washed with water (2×50 mL) followed by brine solution (2×25 mL). The organic layer was concentrated under reduced pressure to obtain 4-fluorobenzaldehyde oxime [Brain, J. Am. Chem. Soc., 133:949-957 (2011)] as white solid (2 g, 61% yield). 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.55 (dd, 2H), 7.06 (t, 2H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. extractionextracted with DCM (2×100 mL)
  3. washthe organic layer washed with water (2×50 mL)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a16cb669e4a9460c9d36a1667bd1d27c
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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