Methanol → N-(4-hydroxy-7-methylquinolin-4-yl)butyramide

HRID 1168765Notes

Reaction equation

HRID 1168765 reaction equation
C([N:3](CC)CC)C.N[C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([CH3:20])[CH:13]=2.[C:21](Cl)(=[O:25])[CH2:22][CH2:23][CH3:24].CO>ClCCl>[OH:19][C:18]1([NH:3][C:21](=[O:25])[CH2:22][CH2:23][CH3:24])[C:17]2[C:12](=[CH:13][C:14]([CH3:20])=[CH:15][CH:16]=2)[N:11]=[CH:10][CH2:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 178422972HCID 178422972, compound

Product 1

HCID 54024046N-(4-hydroxy-7-methylquinolin-4-yl)butyramideYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, triethylamine (0.71 mL, 5.1 mmol) was added to a suspension of 3-amino-7-methyl-4-quinolinol (800 mg, 4.6 mmol) in dichloromethane (30 mL). Butyryl chloride (0.53 mL, 5.1 mmol) was added. The reaction mixture was stirred at ambient temperature for about 2 hours. Analysis by thin layer chromatography (silica gel eluting with 9:1 dichloromethane:methanol) showed starting material. The reaction mixture was heated to reflux and then inadvertently allowed to go dry over the course of about 30 minutes. More solvent was added and the reaction mixture was heated at reflux for an additional hour at which time thin layer chromatography showed no starting material. The resulting precipitate was isolated by filtration and then rinsed with dichloromethane and water to provide 650 mg of N-(4-hydroxy-7-methylquinolin-4-yl)butyramide as a pale pink-tan solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customto go dry over the course of about 30 minutes
  4. additionMore solvent was added
  5. temperaturethe reaction mixture was heated
  6. temperatureat reflux for an additional hour at which time thin layer chromatography
  7. customThe resulting precipitate was isolated by filtration
  8. washrinsed with dichloromethane and water

Sources & evidence

ORD record
ord-389204a5fe5f4deeb8f0ebcf44e0f8e0
Source dataset
uspto-grants-2003_09
Patent number
US06627638B2

Reaction notes

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