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

HRID 2260261Notes

Reaction equation

HRID 2260261 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-cbc6e55f74cc41c4972f9724bd5494bc
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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