Ammonium Hydroxide → 2,8-Dimethylquinolin-7-ol

HRID 338919Notes

Reaction equation

HRID 338919 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].[OH-].[NH4+]>Cl>[CH3:13][C:12]1[CH:11]=[CH:10][C:7]2[C:2](=[C:3]([CH3:9])[C:4]([OH:8])=[CH:5][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 1044482-Amino-o-cresolHCID 447466Crotonaldehyde

Product 1

HCID 1357421682,8-Dimethylquinolin-7-olYield 126.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 3-amino-2-methylphenol (5.0 g, 41 mmol) in refluxing 6N HCl (100 mL) was added dropwise (E)-but-2-enal (5.7 g, 81 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 2,8-dimethylquinolin-7-ol (9.0 g, 51% yield) 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-3476459f4f5b4bc58ace8e97fa4c17e2
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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