Methyl morpholine oxide → 5-Hydroxy-2-methoxypyridine
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C[N+]1([O-])CC[O:16]CC1>ClCCl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([OH:16])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
At RT, 50 g (327 mmol) of 6-methoxypyridin-3-ylboronic acid were added to a solution of 46.0 g (392 mmol) of N-methylmorpholine N-oxide in 500 ml of dichloromethane, and the mixture was stirred at 50° C. for 14 h. Additional N-methylmorpholine N-oxide was added until the reaction had gone to completion. The reaction mixture was concentrated under reduced pressure and the crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate mixtures). Yield: 32.9 g (80% of theory)
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate mixtures)
Sources & evidence
- ORD record
- ord-873065e9d4b141dcac24f012c4cf7220
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434690B2
Reaction notes
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