Triethylamine → HCID 57447109, compound

HRID 2366718Notes

Reaction equation

HRID 2366718 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:20](Cl)(=[O:24])[CH2:21][CH2:22][CH3:23].C(=O)(O)[O-].[Na+]>ClCCl.CO>[Cl:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:8][C:20](=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 516892Sodium BicarbonateHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 57447109HCID 57447109, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (22.3 mL, 0.160 mmol) was added with stirring to a solution of 3-amino-4-chloroquinoline, see Surrey et al., Journal of the American Chemical Society, 73, pp. 2413-2416 (1951), (13.2 g, 74.0 mmol) in anhydrous dichloromethane (100 mL). A solution of butyryl chloride (13 mL, 125 mmol) in dichloromethane (50 mL) was then added dropwise, and the reaction mixture was stirred at ambient temperature overnight. Methanol (25 mL) was added, and the reaction mixture was stirred for one hour at ambient temperature. Saturated aqueous sodium bicarbonate (50 mL) was added, and the resulting mixture was stirred at ambient temperature for 30 minutes and then allowed to stand. The aqueous layer was separated and extracted with dichloromethane (75 mL), and the combined organic fractions were then washed with saturated aqueous sodium bicarbonate (2×50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product (22.8 g) was recrystallized from a mixture of toluene (45 mL) and hexane (15 mL) to provide 9.2 of N-(4-chloroquinolin-3-yl)butanamide as brown needles.

Workup

  1. stirringthe reaction mixture was stirred for one hour at ambient temperature
  2. stirringthe resulting mixture was stirred at ambient temperature for 30 minutes
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (75 mL)
  5. washthe combined organic fractions were then washed with saturated aqueous sodium bicarbonate (2×50 mL)
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product (22.8 g) was recrystallized from a mixture of toluene (45 mL) and hexane (15 mL)

Sources & evidence

ORD record
ord-d3388ee2a8474918974c916ff9c2f602
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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