Triethylamine → HCID 57853761, compound

HRID 2105464Notes

Reaction equation

HRID 2105464 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].C(N(CC)CC)C.[NH2:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[Cl:24])=[CH:21][CH:20]=[CH:19][CH:18]=2>ClCCl>[Cl:24][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[NH:13][C:1](=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 57853761HCID 57853761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propionyl chloride (6.32 mL, 1.3 eq) and triethylamine (11.69 mL, 1.5 eq) were added sequentially to a solution of 3-amino-4-chloroquinoline (10.0 g, 1.0 eq) in dichloromethane (200 mL). The reaction mixture was stirred overnight and then quenched with aqueous saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 2% methanol in dichloromethane) to provide 5.8 g of N-(4-chloroquinolin-3-yl)propionamide.

Workup

  1. customquenched with aqueous saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel eluting with 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-619aecd54c554b2fb867d1ab32175cf1
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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