Triethylamine → HCID 57447109, compound

HRID 2105459Notes

Reaction equation

HRID 2105459 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[NH2:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1[Cl:25])=[CH:22][CH:21]=[CH:20][CH:19]=2>ClCCl>[Cl:25][C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[NH:14][C:1](=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 57447109HCID 57447109, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Butyryl chloride (0.72 mL, 6.94 mmol, 1.2 eq.) and triethylamine (1.13 mL, 8.09 mmol, 1.4 eq) were added to a solution of 3-amino-4-chloroquinoline (1.03 g, 5.78 mmol, 1.0 eq) in anhydrous dichloromethane (25 mL). The reaction mixture was stirred at ambient temperature for 3 hours and then washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane) to provide 0.70 g of N-(4-chloroquinolin-3-yl)butyramide.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8e0bf9398d4840369802837136103411
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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