Ammonia → 2-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-amine

HRID 861625Notes

Reaction equation

HRID 861625 reaction equation
O[CH2:2][CH2:3][C:4]1[C:5]([O:11][CH3:12])=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH3:28]>ClCl>[NH2:28][CH2:2][CH2:3][C:4]1[C:5]([O:11][CH3:12])=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 67749Trifluoromethanesulfonic anhydrideHCID 197036802-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-ol

Product 1

HCID 197035762-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

To a solution of 0.20 g (0.8 mmol) of 3-(2-hydroxyethyl)-6-chloro-2-methoxypyridine in 10 ml of dry CH2 Cl2 cooled to -50° C. was added 0.18 ml (0.8 mmol) trifluoromethanesulfonic anhydride under an atmosphere of nitrogen. The mixture was stirred for 30 min at this temperature and an additional 10 min at -78° C. before a rapid addition of 30 ml of cold (-78° C.) NH3 (1). The mixture was stirred for 15 min at room temperature, and then concentrated in vacuo to afford 1.0 g of crude 3-(2-aminoethyl)-6-chloro-2-methoxypyridine as a trifluoromethanesulfonic acid salt.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97f9804e148e4801956ad8188cc2cf23
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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