Ammonium Hydroxide → 6-Fluoro-7-methoxy-2-methylquinoline

HRID 338909Notes

Reaction equation

HRID 338909 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[CH:11](=O)/[CH:12]=[CH:13]/[CH3:14].[OH-].[NH4+]>Cl>[F:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[O:9][CH3:10])[N:6]=[C:13]([CH3:14])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 447466CrotonaldehydeHCID 27745334-Fluoro-3-methoxyaniline

Product 1

HCID 867074426-Fluoro-7-methoxy-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 4-fluoro-3-methoxyaniline (1.0 g, 7.1 mmol) in refluxing 6N HCl (20 mL) was added dropwise (E)-but-2-enal (0.99 g, 14 mmol) and the reaction was heated to reflux for 2 hours. After cooling, the reaction was neutralized with ammonium hydroxide and extracted with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure to yield 6-fluoro-7-methoxy-2-methylquinoline as a brown solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. extractionextracted with DCM
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eafa2ae0f97448f9b45b7affc89921aa
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…