반응 #2025982

반응 방정식

α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol

→

4-amino-α,α-dimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol

수율 82.3%

용매

trifluoroacetic acid

반응 조건

후처리

1. 1
   기타The catalyst was removed by filtration
2. 2
   세척washed with ethanol
3. 3
   농축The filtrate was concentrated under vacuum
4. 4
   workup.DISSOLUTIONThe solid was dissolved in water containing enough hydrochloric acid
5. 5
   기타to form a salt of the product
6. 6
   여과The aqueous solution was filtered through charcoal
7. 7
   기타The resulting precipitate was isolated by filtration
8. 8
   기타dried

실험 절차

A catalytic amount of platinum (IV) oxide was added to a solution of α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol (0.40 g, 1.4 mmole, Example 1) in trifluoroacetic acid (10 mL). The mixture was hydrogenated at 50 psi (3.44×105Pa) for 48 hours. The catalyst was removed by filtration and washed with ethanol. The filtrate was concentrated under vacuum using heptane to azeotrope the trifluoroacetic acid. The resulting oil solidified on standing. The solid was dissolved in water containing enough hydrochloric acid to form a salt of the product. The aqueous solution was filtered through charcoal. The filtrate was made basic with ammonium hydroxide. The resulting precipitate was isolated by filtration and dried to provide 0.3 g of 4-amino-α,α-dimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol as a white solid, m.p. 259.8°-261.3° C. Analysis: Calculated for C14H20N4O: % C, 64.59; % H,7.74; % N, 21.52; Found % C, 64.49; % H, 7.63; % N, 21.41.

출처