Ammonia → HCID 58349476, compound

HRID 1253819Notes

Reaction equation

HRID 1253819 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].N>Cl>[Br:9][C:7]1[CH:6]=[C:5]2[C:3](=[C:2]([F:1])[CH:8]=1)[N:4]=[C:12]([CH3:13])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1230504-Bromo-2-fluoroanilineHCID 447466Crotonaldehyde

Product 1

HCID 58349476HCID 58349476, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Fluoro-4-bromoaniline (10 g, 0.053 mol) was slurried in 6M HCl (100 ml). The mixture was heated to reflux and crotonaldehyde (14.9 g, 0.212 mol) was added dropwise over 1 hour. The resulting mixture was heated for an additional 90 minutes, then cooled down to room temperature and neutralized by careful addition of concentrated ammonia solution. The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography, eluting with 15-10% ethyl acetate/petrol. The product containing fractions were combined and concentrated to ca 60 ml. The product was then isolated by filtration. The filter cake was washed with petrol and air dried to afford the title compound as a solid (5.96 g, 47% yield). 1H NMR (CDCl3, 400 MHz) 2.80 (3H, s), 7.38 (1H, d), 7.53 (1H, d), 7.76 (1H, s), 8.00 (1H, d); MS (ES+) 240/242.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe resulting mixture was heated for an additional 90 minutes
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography
  10. washeluting with 15-10% ethyl acetate/petrol
  11. additionThe product containing fractions
  12. concentrationconcentrated to ca 60 ml
  13. customThe product was then isolated by filtration
  14. washThe filter cake was washed with petrol and air
  15. customdried

Sources & evidence

ORD record
ord-937f5de3847d445bb7314d19a5a25a60
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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