반응 #1948851

반응 방정식

1-isoquinolinecarbonitrile

→

1-(aminomethyl)isoquinoline

용매

acetic acid

반응 조건

후처리

1. 1
   여과the reaction mixture was filtered over celite
2. 2
   세척The celite was washed with 75 mL EtOAc
3. 3
   농축the filtrate was concentrated in vacuo
4. 4
   workup.ADDITIONTo this was added 100 mL n-heptane
5. 5
   농축the mixture concentrated in vacuo
6. 6
   기타to remove acetic acid
7. 7
   기타Purification by flash chromatography (40×220 mm silica gel, linear gradient 5-10% (10% NH4OH:MeOH):CH2C12)
8. 8
   기타yielded 2

실험 절차

To a solution of 0.4999 g (3.24 mmol) 1-isoquinolinecarbonitrile (1) (Aldrich) in 15 mL glacial acetic acid was added 0.0564 g Pd (10% on C). After 16 h under H2 at atmospheric pressure, the reaction mixture was filtered over celite. The celite was washed with 75 mL EtOAc, and the filtrate was concentrated in vacuo. To this was added 100 mL n-heptane, and the mixture concentrated in vacuo. The above step was repeated three times to remove acetic acid. Purification by flash chromatography (40×220 mm silica gel, linear gradient 5-10% (10% NH4OH:MeOH):CH2C12) yielded 2. 1H NMR (CDCl3, 400 MHz) δ 8.479 (d, 1H, J=5.76 Hz, ArH); 8.135 (d, 1H, J=8.42 Hz, ArH); 7.848 (d, 1H, J=8.41 Hz, ArH); 7.714-7.673 (m, 1H, ArH); 7.639-7.597 (m, 1H, ArH); 7.563 (d, 1H, J=5.67 Hz, ArH); 4.517 (s, 2H, ArCH2); MS (FAB): m/z 159.08 (M30 H).

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