Ammonium Hydroxide → 3-Butyl-4-chloro quinoline

HRID 1110114Notes

Reaction equation

HRID 1110114 reaction equation
[CH2:1]([C:5]1[C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:18])=O.[OH-].[NH4+]>O>[CH2:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:18])=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 195953413-butyl-4-(1H)-quinolinone

Product 1

HCID 195953523-Butyl-4-chloro quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 515 mg of the product of Step E and 0.6 ml of phosphorous oxychloride was heated for 2 hours at 120° C. and the mixture was cooled. 10 ml of water were added and the solution was alkalized to pH 9 with concentrated ammonium hydroxide. Extraction was carried out twice with methylene chloride and the extracts were washed with a saturated solution of sodium chloride, dried and evaporated to dryness. The residue was dissolved in 30 ml of ethanol and treated for 15 minutes at reflux in the presence of activated charcoal, followed by filtering on hyflosupercel to obtain 511 mg of the desired product.

Workup

  1. temperaturethe mixture was cooled
  2. extractionExtraction
  3. washthe extracts were washed with a saturated solution of sodium chloride
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in 30 ml of ethanol
  7. additiontreated for 15 minutes
  8. temperatureat reflux in the presence of activated charcoal
  9. filtrationby filtering on hyflosupercel

Sources & evidence

ORD record
ord-f1bf86ee7f4e4bf5af38417b4e0448c3
Source dataset
uspto-grants-1994_06
Patent number
US05324839

Reaction notes

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