Sodium Hydroxide → HCID 178491837, compound

HRID 1963006Notes

Reaction equation

HRID 1963006 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5].Cl.[NH2:14][OH:15].[OH-].[Na+]>CCO>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([F:12])[C:3]=1[C:4]([NH:14][OH:15])=[NH:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 37918322,6-Difluoro-3-methoxybenzonitrile

Product 1

HCID 178491837HCID 178491837, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,6-difluoro-3-methoxybenzonitrile (0.30 g, 1.70 mmol) in EtOH (10 ml) was added hydroxylamine hydrochloride (0.12 g, 1.70 mmol) and NaOH (0.071 g, 1.70 mmol). The resulting reaction mixture was refluxed for 15 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added EtOH and filtered. The filtrate was evaporated in vacuo and the crude residue was purified over silica gel (60-120 M, 30% EtOAc-Hexane) to get the desired product (0.15 g, 42%) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 15 h
  3. customAfter the completion of the reaction (TLC monitoring)
  4. concentrationthe mixture was concentrated
  5. additionadded EtOH
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe crude residue was purified over silica gel (60-120 M, 30% EtOAc-Hexane)

Sources & evidence

ORD record
ord-4b8a3b32071b4f4ba96b0764b952141f
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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