Triethylamine → HCID 66765094, compound

HRID 2105491Notes

Reaction equation

HRID 2105491 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[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(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[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:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 516892Sodium BicarbonateHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 66765094HCID 66765094, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of valeryl chloride (13.3 mL, 112 mmol) in dichloromethane (35 mL) was added dropwise to a stirred solution of 3-amino-4-chloroquinoline (10.0 g, 56 mmol) and triethylamine (2.1 mL, 15 mmol) in dichloromethane (100 mL), and the reaction was stirred overnight at room temperature and then stirred for one hour with saturated aqueous sodium bicarbonate (150 mL). The aqueous layer was separated and extracted with dichloromethane (2×50 mL). The combined organic fractions were washed with saturated aqueous sodium bicarbonate (50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure. The residue was recrystallized from toluene/hexane to provide 11.1 g of N-(4-chloroquinolin-3-yl)pentanamide as a light brown solid.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane (2×50 mL)
  3. washThe combined organic fractions were washed with saturated aqueous sodium bicarbonate (50 mL)
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-0b7052ed7b814e998822e833a594569c
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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