Ammonia → 3-Amino-2-(p-fluorobenzoyl)crotononitrile

HRID 46563Notes

Reaction equation

HRID 46563 reaction equation
[NH3:1].[Na].[F:3][C:4]1[CH:18]=[CH:17][C:7]([C:8](/[C:10](=[C:13](/OC)\[CH3:14])/[C:11]#[N:12])=[O:9])=[CH:6][CH:5]=1>>[NH2:1]/[C:13](/[CH3:14])=[C:10](/[C:8](=[O:9])[C:7]1[CH:17]=[CH:18][C:4]([F:3])=[CH:5][CH:6]=1)\[C:11]#[N:12]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 234685082-(p-Fluorobenzoyl)-3-methoxycrotononitrile

Product 1

HCID 203874923-Amino-2-(p-fluorobenzoyl)crotononitrile

Procedure

Approximately 50 ml. of liquid ammonia is condensed in a three-neck flask cooled to -78° in a dry ice-acetone bath. To this is added 200 mg. of sodium metal, followed by 100 mg. of ferric chloride hexahydrate. When the blue color had vanished, 6.2 g. of 2-(p-fluorobenzoyl)-3-methoxycrotononitrile is added. After stirring for one hour, the reaction is allowed to warm and the solvent evaporate. The residue is dissolved in hot ethyl acetate and filtered through Celite®. The filtrate is concentrated on the steam bath and diluted with hexane. Upon cooling, the crystalline product precipitates, is filtered and dried.

Workup

  1. customcondensed in a three-neck flask
  2. temperaturecooled to -78° in a dry ice-acetone bath
  3. additionTo this is added 200 mg
  4. temperatureto warm
  5. customthe solvent evaporate
  6. dissolutionThe residue is dissolved in hot ethyl acetate
  7. filtrationfiltered through Celite®
  8. concentrationThe filtrate is concentrated on the steam bath
  9. additiondiluted with hexane
  10. temperatureUpon cooling
  11. customthe crystalline product precipitates
  12. filtrationis filtered
  13. customdried

Sources & evidence

ORD record
ord-59bcf75c2403407582618fb4d89fa628
Source dataset
uspto-grants-1979_11
Patent number
US04173650

Reaction notes

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