Ammonium Hydroxide → HCID 70983878, compound

HRID 338972Notes

Reaction equation

HRID 338972 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].[OH-].[NH4+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:6]([CH:10]=[CH:11][C:12]([CH3:13])=[N:5]2)=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 447466CrotonaldehydeHCID 27792863-Bromo-4-fluoroaniline

Product 1

HCID 70983878HCID 70983878, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
106 °C

Procedure

To a solution of 3-bromo-4-fluoroaniline (10.00 g, 52.63 mmol) in 6N HCl (150 mL) was added (E)-but-2-enal (7.524 mL, 92.10 mmol) dropwise over 10 minutes at 106° C. The reaction was stirred at 106° C. for 2 hours. After cooling to ambient temperature, the reaction mixture was basified with ammonium hydroxide to about pH 12, extracted with DCM (2×100 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 5:1) to give 7-bromo-6-fluoro-2-methylquinoline (3.26 g, 25.8%) as a solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with DCM (2×100 mL)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-4abe69c73301442cabd2ba0972c5aaca
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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