Hydrogen Bromide → 5-Cyclopropyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde
Reaction equation
Br.[CH:2]1([C:5]2[CH:6]=[CH:7][C:8]([CH:13]=[O:14])=[N:9][C:10]=2[O:11]C)[CH2:4][CH2:3]1.O>O1CCOCC1>[CH:2]1([C:5]2[C:10](=[O:11])[NH:9][C:8]([CH:13]=[O:14])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
48% hydrobromic acid (3 mL) was added to a solution of 5-cyclopropyl-6-methoxypyridine-2-carbaldehyde obtained in Reference Example 1-51(6) (437 mg) in 1,4-dioxane (6 mL), and the mixture was stirred at 65° C. for two hours. The reaction solution was poured into water, followed by extraction with chloroform/methanol (2:1). The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25→0:100) to give 5-cyclopropyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde as a yellow powder (278 mg, 69%).
Workup
- extractionfollowed by extraction with chloroform/methanol (2:1)
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25→0:100)
Sources & evidence
- ORD record
- ord-2587d6c306a1442c9072ff8eae4aabc5
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822503B2
Reaction notes
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