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

HRID 338928Notes

Reaction equation

HRID 338928 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].[NH4+].[OH-]>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-methylquinolineYield 97.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 4-fluoro-3-methoxyaniline (4.0 g, 28 mmol) refluxing in 6N HCl (50 mL) was added dropwise (E)-but-2-enal (4.0 g, 57 mmol). The reaction was heated to reflux for 2 hours then cooled and neutralized with NH4OH. The organic phase was extracted with DCM. The combined organic phases dried over MgSO4, filtered and concentrated under reduced pressure to provide 6-fluoro-7-methoxy-2-methylquinoline (5.2 g, 96% yield) as a dark brown paste.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen cooled
  4. extractionThe organic phase was extracted with DCM
  5. dry with materialThe combined organic phases dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81cbd557125b4fc397eb629fe3092263
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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