Methanol → 4-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 924398노트

반응식

HRID 924398 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=12.[CH3:11][OH:12].C[O-].[Na+]>CCOC(C)=O.Cl>[CH3:11][O:12][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=12

참가 물질

6

반응물 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 122033274-chloro-5H,6H,7H-cyclopenta[b]pyridine

생성물 1

HCID 867266834-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine수율 44%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

A mixture of 4-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (2.8 g, 18 mmol), MeOH (20 mL) and sodium methoxide (3.0 g, 56 mmol) was sealed in a pressurized flask and heated at 110° C. for 18 h. The mixture was diluted with EtOAc and neutralized with HCl to pH=1. The organic solvent was removed under reduced pressure. The resulting mixture was washed with ether twice, and neutralized with aq. Na2CO3. The aqueous layer was extracted twice with EtOAc. The combined organic extracts were dried, filtered and concentrated under reduced pressure to give the sub-title compound (1.20 g, 44%). LCMS calc. for C9H12NO (M+H)+: m/z=150.3. Found: 150.2.

후처리

  1. customwas sealed in a pressurized flask
  2. customThe organic solvent was removed under reduced pressure
  3. washThe resulting mixture was washed with ether twice
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-001833d127c343ab84b58eecb4e33c70
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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