Reaction #992697

Reaction equation

aniline

1-naphthoyl chloride

water

ammonium hydroxide

→

solid

Yield 82.0%

Naphthalene-1-carboxylic acid phenylamide

Yield 82.0%

Solvents

acetonitrile

diethyl ether

Conditions

Workup

1. 1
   OtherTo the solution so formed
2. 2
   Other20 min
3. 3
   OtherThe phases were separated
4. 4
   Washthe aqueous phase was washed with 100 ml of dichloromethane
5. 5
   OtherThe organic fractions were collected
6. 6
   Dryingdried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Otherthe solvent was then removed under reduced pressure

Procedure

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