Methanol → 2-Methoxy-5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridine-3-carbaldehyde
反応式
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=C)[N:9]([CH3:15])[C:8](=[O:16])[CH2:7][CH2:6]2.C[OH:18]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]([CH:13]=[O:18])=[CH:11][C:10]2[N:9]([CH3:15])[C:8](=[O:16])[CH2:7][CH2:6][C:5]=2[N:4]=1参加物
反応条件
- 温度
- -70 °C
実験手順
A 1.1 g (5.0 mmol) solution of 6-methoxy-1-methyl-7-vinyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one in 50 ml of methylene chloride and 10 ml of methanol was cooled to −70° C. Ozone (via an ozone generator) was bubbled into the solution until a blue color was achieved. The reaction mixture was stirred at −70° C. for 30 minutes and quenched with 4.0 ml of dimethyl sulfide. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into 50 ml of water. The organic layer was dried (Na2SO4) and evaporated. This residue was chromatographed on silica using 10:1 chloroform/ethyl acetate as the elutant. Appropriate fractions were combined to yield 0.52 g of 2-methoxy-5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridine-3-carbaldehyde. TLC Rf=0.4 (1:1 ethyl acetate:hexane). 1H NMR (CDCl3) δ 10.18 (s, 1H), 7.7 (s, 1H), 4.05 (s, 3H), 3.3 (s, 3H), 3.0 (m, 2H), 2.7 (m, 2H). Mass spectrum: m/e=221.1, (p+1).
後処理
- customOzone (via an ozone generator) was bubbled into the solution until a blue color
- customquenched with 4.0 ml of dimethyl sulfide
- stirringThe reaction mixture was stirred for 18 hours at room temperature
- additionThe reaction mixture was poured into 50 ml of water
- dry with materialThe organic layer was dried (Na2SO4)
- customevaporated
- customThis residue was chromatographed on silica using 10:1 chloroform/ethyl acetate as the elutant
出典と根拠
- ORDレコード
- ord-69dd668f26ed401483ca072142660720
- 出典データセット
- uspto-grants-2006_10
- 特許番号
- US07119207B2
反応ノート
読み込み中…