Hydrochloric Acid → 4-{[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}aniline

HRID 637987Notes

Reaction equation

HRID 637987 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(O)(C)C.Cl>[Fe].O>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 27757362-(4-Nitrophenoxy)-3-chloro-5-trifluoromethyl pyridine

Product 1

HCID 27641164-{[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}anilineYield 80.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-chloro-5-trifluoromethyl-2-(4-nitrophenoxy)pyridine (1.0 g), iron powder (3.2 g), isopropyl alcohol (60 ml), water (6 ml) and dilute hydrochloric acid (0.2 ml of a 2N solution), were heated at the reflux temperature for 12 hours. After cooling and filtering to remove the solid matter, the filtrate was concentrated by evaporation of the volatile portion under reduced pressure. The residual solid was recrystallised from n-hexane to yield 2-(4-aminophenoxy)-3-chloro-5-trifluoromethylpyridine (0.73 g) m.p. 85°-87° C.

Workup

  1. temperaturewere heated at the reflux temperature for 12 hours
  2. temperatureAfter cooling
  3. filtrationfiltering
  4. customto remove the solid matter
  5. concentrationthe filtrate was concentrated by evaporation of the volatile portion under reduced pressure
  6. customThe residual solid was recrystallised from n-hexane

Sources & evidence

ORD record
ord-955ff5a690e846b3a309b3bf2db62aad
Source dataset
uspto-grants-1985_12
Patent number
US04559353

Reaction notes

Loading…