Réaction #992697

Équation de réaction

aniline

1-naphthoyl chloride

water

ammonium hydroxide

→

solid

Rendement 82.0%

Naphthalene-1-carboxylic acid phenylamide

Rendement 82.0%

Solvants

acetonitrile

diethyl ether

Conditions de réaction

Traitement

1. 1
   AutreTo the solution so formed
2. 2
   Autre20 min
3. 3
   AutreThe phases were separated
4. 4
   Lavagethe aqueous phase was washed with 100 ml of dichloromethane
5. 5
   AutreThe organic fractions were collected
6. 6
   Séchagedried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Autrethe solvent was then removed under reduced pressure

Mode opératoire

4.77 g of 1-naphthoyl chloride (TCI America) was dissolved in 100 ml of anhydrous acetonitrile. To the solution so formed, 2.28 ml of aniline (Sigma-Aldrich) was added in a dropwise fashion over a period of c.a. 20 min. The reaction was then refluxed for 2 h at 82° C. 100 ml of distilled water and 5 ml of concentrated ammonium hydroxide were added along with 100 ml of diethyl ether in a separatory funnel. The phases were separated and the aqueous phase was washed with 100 ml of dichloromethane. The organic fractions were collected and dried with magnesium sulfate, filtered and the solvent was then removed under reduced pressure to yield a white solid 5.07 g (82%; 20.5 mmol).

Source