Hydrogen Bromide → 3-Nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-ol
Reaction equation
C[O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]2[CH2:12][CH2:13][CH2:14][C:4]=12.Br>CC(O)=O>[N+:9]([C:8]1[C:3]([OH:2])=[C:4]2[CH2:14][CH2:13][CH2:12][C:5]2=[N:6][CH:7]=1)([O-:11])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 4-methoxy-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (1.535 g, 7.905 mmol) in AcOH (2.6 mL) was treated with 48% aq. HBr (2.6 mL, 23 mmol). The flask was sealed and heated at 130° C. for 40 min. then allowed to cool. The mixture was then concentrated under reduced pressure and the residue was neutralized to pH=7-8 using 50% NaOH in a cold bath. The mixture was then concentrated under reduced pressure and the residue was diluted with MeOH and THF, dried, filtered and concentrated to give the sub-title compound as a light brown powder. LCMS calc. for C8H9N2O3(M+H)+: m/z=181.3. Found: 181.2.
Workup
- customThe flask was sealed
- temperatureto cool
- concentrationThe mixture was then concentrated under reduced pressure
- concentrationThe mixture was then concentrated under reduced pressure
- additionthe residue was diluted with MeOH and THF
- customdried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b82360d12a5f4568926b52503c412d5e
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278950B2
Reaction notes
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