Potassium Carbonate → 3-chloro-4-fluoro-N-hydroxy-benzenecarboximidamide

HRID 1898338Notes

Reaction equation

HRID 1898338 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[C:5]#[N:6].Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[C:5](=[N:12][OH:13])[NH2:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1455253-Chloro-4-fluorobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 44117393-chloro-4-fluoro-N-hydroxy-benzenecarboximidamideYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-chloro-4-fluoro benzonitrile (1.0 g, 6.42 mmol) in ethanol (20 mL), was added hydroxylamine hydrochloride (0.665 g, 9.64 mmol), followed by addition of potassium carbonate (2.66 g, 19.28 mmol). The reaction mass was refluxed for 10-12 h. Excess of solvent was removed under vacuum and the reaction mass was diluted with water, acidified with dilute HCl and filtered to afford 0.400 g the desired product. 1HNMR (DMSO-d6): δ 5.95 (s, 2H), 7.42 (t, J=8.7 Hz, 1H), 7.69 (m, 1H), 7.83 (dd, 1H), 9.80 (s, 1H); MS [M+H]+: 189.12.

Workup

  1. temperatureThe reaction mass was refluxed for 10-12 h
  2. customExcess of solvent was removed under vacuum
  3. additionthe reaction mass was diluted with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-36acf960d3d74ebebcb1373c0a3a480a
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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