Trichloroacetic Acid → 3,4-dihydro-5-methyl-1(2H)-isoquinolinone

반응식

[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].ClC(Cl)(Cl)C(O)=O.[N-:19]=[N+]=[N-].[Na+]>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:19][C:6]2=[O:11]

참가 물질

반응물 3

HCID 6421Trichloroacetic Acid

HCID 33557Sodium Azide2회

HCID 44184314-Methyl-1-indanone

생성물 1

HCID 1481403,4-dihydro-5-methyl-1(2H)-isoquinolinone수율 47.2%

실험 절차

A mixture of 4.7 g (32.2 mmol) of 2,3-dihydro-4-methyl-1H-inden-1-one and 53 g of trichloroacetic acid was heated to 65°. To the resulting solution was added 4.2 g (64.4 mmol) of sodium azide and the mixture was kept at 65° for 18 hours. An additional 1.0 g of sodium azide was then added and heating continued for another four hours. The mixture was diluted with 200 ml of ice water and extracted with ether. The ether extracts were washed with water, saturated sodium hydrogen carbonate, dried (MgSO4), and concentrated. The residue was chromatographed (SiO2, ether to ether/methanol 95/5). The resulting product was recrystallized from toluene to give 2.45 g (47%) of product; mp 141°-143°.