Hydrochloric Acid → 110860-87-2

HRID 845176Notes

Reaction equation

HRID 845176 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:18])([F:17])[CH:14]([Cl:16])[F:15])=[CH:8][N:7]=1.[OH-].[K+].[ClH:21]>O>[Cl:21][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:18])([F:17])[CH:14]([Cl:16])[F:15])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14665031HCID 14665031, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14665048110860-87-2Yield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 7.59 g (0.11 mol) of sodium nitrite in 15 ml of water was added dropwise with stirring to a solution of 22.6 g (0.1 mol) of 2-amino-5-(2-chloro-1,1,2-trifluoroethoxy)pyridine in 100 ml of concentrated HCl at 0° C. The mixture was stirred for one hour at 50° C., the pH was adjusted to 6.5 using 2N KOH, and the product was extracted three times with 100 ml of dichloromethane in each case. After drying over sodium sulfate and removal of the solvent by evaporation on a rotary evaporator, the residue was distilled at 6.5 mbar and 13 g of 2-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)pyridine were obtained as a colorless liquid.

Workup

  1. extractionthe product was extracted three times with 100 ml of dichloromethane in each case
  2. dry with materialAfter drying over sodium sulfate and removal of the solvent by evaporation on a rotary evaporator
  3. distillationthe residue was distilled at 6.5 mbar

Sources & evidence

ORD record
ord-e4eb7a5f94a64e5ea5dfc7d44c0f353a
Source dataset
uspto-grants-1988_07
Patent number
US04756739

Reaction notes

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