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

HRID 924398Notes

Reaction equation

HRID 924398 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-001833d127c343ab84b58eecb4e33c70
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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