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

HRID 1499439노트

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HRID 1499439 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 then neutralized with Na2CO3 solution. The aqueous layer was extracted twice with EtOAc. The combined organic layers 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=150.1. 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 layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c9c30d8c57d94708b00078f53a59c81f
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200004B2

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