Ammonia → HCID 19703271, compound

HRID 233732Notes

Reaction equation

HRID 233732 reaction equation
O[CH2:2][CH2:3][C:4]1[C:5]([F:10])=[N:6][CH:7]=[CH:8][CH:9]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH3:26]>C(Cl)Cl>[NH2:26][CH2:2][CH2:3][C:4]1[C:5]([F:10])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 67749Trifluoromethanesulfonic anhydrideHCID 197036682-(2-Fluoropyridin-3-yl)ethanol

Product 1

HCID 19703271HCID 19703271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 0.20 g (1.42 mmol) of 3-(2-hydroxyethyl)-2-fluoropyridine in 8 ml of dry CH2Cl2 cooled to -40° C. was added 0.18 ml (0.8 mmol) trifluoromethanesulfonic anhydride under an atmosphere of nitrogen. After stirring for 30 min at -40° C., 30 ml of cold (-78° C.) NH3 (l) was added. The mixture was stirred for 30 min at -40° C., and then concentrated in vacuo to afford 1.03 g of crude salt which was washed twice with 20 ml diethyl ether to yield 0.82 g of 3-(2-aminoethyl)-2-fluoropyridine as a trifluoromethanesulfonic acid salt.

Workup

  1. stirringThe mixture was stirred for 30 min at -40° C.
  2. concentrationconcentrated in vacuo
  3. customto afford 1.03 g of crude salt which
  4. washwas washed twice with 20 ml diethyl ether

Sources & evidence

ORD record
ord-41febb70df5e40fba6f34fd644d46cdf
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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