Acetic Anhydride → Acetamide, N-[2-(4-chlorophenyl)ethyl]-N-(8-fluoro-4-quinolinyl)-

HRID 1196469Notes

Reaction equation

HRID 1196469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[C:16]([F:21])[CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([C:11]2[C:20]3[C:15](=[C:16]([F:21])[CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[C:22](=[O:24])[CH3:23])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 164180N-[2-(4-Chlorophenyl)ethyl]-8-fluoroquinolin-4-amine

Product 1

HCID 164179Acetamide, N-[2-(4-chlorophenyl)ethyl]-N-(8-fluoro-4-quinolinyl)-

Procedure

A mixture of 2.0 g of N-[2-(4-chlorophenyl)ethyl]-8-fluoro-4-quinolinamine and 5.0 mL of acetic anhydride was refluxed overnight. The mixture was then cooled, and solvents were removed by reducing pressure. The residue was washed with water and then dried. The resulting oil was passed over a silica gel column with ethyl acetate, and the front running spot was collected, producing 0.8 g of the title product as a thick oil.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe mixture was then cooled
  3. customsolvents were removed
  4. washThe residue was washed with water
  5. customdried
  6. customwas collected

Sources & evidence

ORD record
ord-76a3137aaf214e2984966b49ea48ad33
Source dataset
uspto-grants-1992_05
Patent number
US05114939

Reaction notes

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