Pyridine → HCID 86245269, compound

HRID 2263060Notes

Reaction equation

HRID 2263060 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18]>O1CCCC1>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:17](=[O:18])[O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 811216-Methoxy-3-pyridinylamineHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 86245269HCID 86245269, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-2-methoxypyridine (1.00 g, 8.06 mmol) and pyridine (1.96 ml, 24.2 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.67 ml, 12.1 mmol) with ice-cooling, the mixture was stirred for 30 minutes with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the desired product (2.30 g, 95.4%) as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5a4b0072bc974f17954edd84775fe5e2
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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