Boron trifluoride → 2-Amino-3-methoxypyridine

HRID 1740931Notes

Reaction equation

HRID 1740931 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][Si](C=[N+]=[N-])(C)C.B(F)(F)F>CO.C1C=CC=CC=1>[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 281142-Amino-3-HydroxypyridineHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 99203842-Amino-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

A solution of 2-amino-3-hydroxypyridine (Aldrich, 200 mg) in 20% methanol/benzene (4 mL) was treated with trimethylsilyldiazomethane (1.8 mL, 2.0 M), boron trifluoride diethyletherate (0.026 mL) and stirred at room temperature for 16 hr. The solvent was evaporated in vacuo and the crude oil was purified by medium pressure liquid chromatography on a 21×300 mm silica column eluted with 50% ethyl acetate/lmethylene chloride to give the title compound (50 mg).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude oil was purified by medium pressure liquid chromatography on a 21×300 mm silica column
  3. washeluted with 50% ethyl acetate/lmethylene chloride

Sources & evidence

ORD record
ord-ded8f6a1360145878a904bd8d8d4d55a
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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