Potassium Carbonate → HCID 178513323, compound

HRID 59257Notes

Reaction equation

HRID 59257 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[OH:11][NH2:12].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[NH:7])[NH:12][OH:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513323HCID 178513323, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-fluorobenzonitrile (0.500 g, 4.13 mmol) in ethanol (3 mL) was added hydroxyl amine HCl (0.427 g, 6.19 mmol) and potassium carbonate (1.14 g, 8.26 mmol). The reaction mass was stirred at RT for 15-17 h. Excess of solvent was removed under vacuum. The obtained residue was diluted with water, acidified with dilute HCl and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.450 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 5.84 (br s, 2H), 7.17-7.27 (m, 2H), 7.68-7.73 (m, 2H), 9.64 (br s, 1H); MS (m/z): 155.13 (M+H)+.

Workup

  1. customExcess of solvent was removed under vacuum
  2. additionThe obtained residue was diluted with water
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef9c0e94012d4d2d966e296f0dc14ec4
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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