Hydrochloric Acid → N-(3,5-dichloro-2-pyridyl)-2,6-dinitro-4-trifluoromethylaniline

HRID 1065771Notes

Reaction equation

HRID 1065771 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH-].[K+].[N+:12]([C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([N+:25]([O-:27])=[O:26])[C:16]=1Cl)([O-:14])=[O:13].Cl>CN(C)C=O>[Cl:8][C:7]1[C:2]([NH:1][C:16]2[C:17]([N+:25]([O-:27])=[O:26])=[CH:18][C:19]([C:21]([F:24])([F:22])[F:23])=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 14797Potassium HydroxideHCID 778863,5-Dichloro-3-pyridylamine

Product 1

HCID 12812456N-(3,5-dichloro-2-pyridyl)-2,6-dinitro-4-trifluoromethylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml. of dimethylformamide, 1.65 g. of 2-amino-3,5-dichloropyridine was dissolved and 1.0 g. of powdery potassium hydroxide was gradually added with stirring. After the addition, 2.7 g. of 2,6-dinitro-4-trifluoromethylchlorobenzene was added at 30° C. during 5 minutes and the reaction was continued for about 3 hours. The reaction mixture was acidified with conc. HCl and the product was extracted with methylenechloride. The extracted layer was washed with water and dehydrated. The solvent was distilled off and the product was separated by a silica gel column with an eluent of toluene and the solvent was distilled off to obtain 2.8 g. of the object compound having the melting point of 85° to 87° C.

Workup

  1. additionAfter the addition, 2.7 g
  2. extractionthe product was extracted with methylenechloride
  3. washThe extracted layer was washed with water
  4. distillationThe solvent was distilled off
  5. customthe product was separated by a silica gel column with an eluent of toluene
  6. distillationthe solvent was distilled off
  7. customto obtain 2.8 g

Sources & evidence

ORD record
ord-1af14dcdaf7e4490a38784b68f83c817
Source dataset
uspto-grants-1982_05
Patent number
US04331670

Reaction notes

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