Hydroxyamine hydrochloride → 2-Fluoro-3,4-dimethoxybenzonitrile

HRID 1781850Notes

Reaction equation

HRID 1781850 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:15]O>C(O)C>[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 6035882-Fluoro-3,4-dimethoxybenzaldehyde

Product 1

HCID 214590582-Fluoro-3,4-dimethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 g of 2-fluoro-3,4-dimethoxybenzaldehyde and 1.83 g of hydroxylamine hydrochloride are heated under reflux for 5 hours together with 30 ml of ethanol. The reaction mixture is subsequently evaporated and the residue, dried in a high vacuum at 23°, is introduced into 40 ml of phosphorus oxychloride. After stirring at 23° for 2.5 hours the reaction mixture is evaporated, the residue is treated with ice-water, the precipitate which thereby forms is filtered off, washed with water, taken up in methylene chloride, the methylene chloride solution is dried over sodium sulfate and evaporated. By recrystallization of the residue from methylene chloride/hexane there is obtained 2-fluoro-3,4-dimethoxybenzonitrile of m.p. 64°-65°.

Workup

  1. customThe reaction mixture is subsequently evaporated
  2. customthe residue, dried in a high vacuum at 23°
  3. additionis introduced into 40 ml of phosphorus oxychloride
  4. customis evaporated
  5. additionthe residue is treated with ice-water
  6. filtrationthe precipitate which thereby forms is filtered off
  7. washwashed with water
  8. dry with materialthe methylene chloride solution is dried over sodium sulfate
  9. customevaporated
  10. customBy recrystallization of the residue from methylene chloride/hexane there

Sources & evidence

ORD record
ord-10c5c9c0dee84189a6ffec9f42984a0c
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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