Methyl morpholine oxide → 5-Hydroxy-2-methoxypyridine

HRID 56749

Reaction equation

HRID 56749 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]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 2734368(6-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 116223355-Hydroxy-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. 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

Linked notes

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