Acetyl chloride → N-(6-Bromo-quinolin-2-ylmethyl)-acetamide

HRID 2075680Notes

Reaction equation

HRID 2075680 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][NH2:13])[CH:6]=[CH:5]2.CCN(CC)CC.[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][NH:13][C:21](=[O:23])[CH3:22])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57365264(6-Bromoquinolin-2-YL)methanamine

Product 1

HCID 67091079N-(6-Bromo-quinolin-2-ylmethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 4b (401 mg, 1.7 mmol) in CH2Cl2 at room temperature was added NEt3 (0.47 mL, 3.4 mmol), followed by acetyl chloride (0.18 mL, 2.6 mmol). Once the reaction was complete by LCMS analysis, the mixture was concentrated and purified by silica gel chromatography (0-100% EtOAc in hexanes, followed by 10% MeOH in EtOAc) to give the desired product, 4c.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel chromatography (0-100% EtOAc in hexanes, followed by 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-79e60b44f3d14657b94e83c31a15ac05
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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