Hydrochloric Acid → HCID 67135536, compound

HRID 1896636Notes

Reaction equation

HRID 1896636 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.Cl>C(O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:15])([F:16])[F:14])=[N:4][CH:5]=[C:6]([NH2:8])[CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67135451HCID 67135451, compound

Product 1

HCID 67135536HCID 67135536, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Chloro-5-nitro-2-(2,2,2-trifluoroethoxy)-pyridine (5.39 g) obtained in Step A was reduced with iron (13.6 g) and concentrated hydrochloric acid (0.73 ml) in ethanol (6.5 ml) and water (1 ml) at 80° C. for 1 hour. Filtration over Celite® and evaporation of the solvent followed by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 9:1) afforded 3-chloro-5-amino-2-(2,2,2-trifluoro-ethoxy)-pyridine (3.1 g).

Workup

  1. filtrationFiltration
  2. customover Celite® and evaporation of the solvent

Sources & evidence

ORD record
ord-78178088b6da43a688c644f74485ec48
Source dataset
uspto-grants-2013_08
Patent number
US08518971B2

Reaction notes

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