Sulfuric Acid → 4-Methoxy-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine
반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=12.S(=O)(=O)(O)O.[N+:17]([O-])([O-:19])=[O:18].[K+].[OH-].[Na+]>>[CH3:1][O:2][C:3]1[C:8]([N+:17]([O-:19])=[O:18])=[CH:7][N:6]=[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=12참가 물질
반응 조건
- 온도
- 80 °C
실험 절차
4-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine (2.90 g, 19.4 mmol) was mixed with concentrated sulfuric acid (17.0 g, 173 mmol) at 0° C., then a mixture of potassium nitrate (5.3 g, 52 mmol) in another portion of concentrated sulfuric acid (26.5 g, 270 mmol) was added slowly. The reaction mixture was heated at 80° C. for 4 h. The crude mixture was slowly poured onto crushed ice (50 g), and neutralized carefully with 50% aq. NaOH to pH 8-9. The resulting mixture was extracted with EtOAc five times. The combined organic extracts were dried and concentrated under reduced pressure to give the crude sub-title compound as brown gum (1.56 g, 41%), which was used without further purification. LCMS calc. for C9H11N2O3 (M+H)+: m/z=195.1. Found: 195.2.
후처리
- additionwas added slowly
- extractionThe resulting mixture was extracted with EtOAc five times
- customThe combined organic extracts were dried
- concentrationconcentrated under reduced pressure
출처 및 근거
- ORD 기록
- ord-3f31aa18dc5640afbb9175096ca781c8
- 출처 데이터셋
- uspto-grants-2015_12
- 특허 번호
- US09200004B2
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