Reaction #1605

Reaction equation

ammonium chloride

quinolinone

NaH

1-bromo-2-pentyne

→

product

5-chloro-1-(2-pentyn-1-yl)-2-quinolinone

Solvents

DMF

hexane

Conditions

Workup

1. 1
   workup.WAITThe resulting mixture was kept at 0° C. for one half hour
2. 2
   ExtractionThe aqueous suspension was extracted with ether (3×100 ml)
3. 3
   Washthe combined ether layers washed with brine
4. 4
   Otherdried
5. 5
   Otheryielding the crude product

Procedure

To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid (1 g).

Source