Acetyl chloride → HCID 67506066, compound

HRID 2105467Notes

Reaction equation

HRID 2105467 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH2:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[Cl:23])=[CH:20][CH:19]=[CH:18][CH:17]=2>ClCCl>[Cl:23][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:12][C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 67506066HCID 67506066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (3.41 mL, 1.25 eq) and triethylamine (6.79 mL, 1.4 eq) were added sequentially to a solution of 3-amino-4-chloroquinoline (6.22 g, 1.0 eq) in dichloromethane (100 mL). The reaction mixture was stirred overnight and then washed sequentially with aqueous saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated under reduced pressure to provide 6.68 g of N-(4-chloroquinolin-3-yl)acetamide.

Workup

  1. washwashed sequentially with aqueous saturated sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88fb07731972457abaac6396ee3161b9
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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