Hydrochloric Acid → 3-Amino-6-(3,5-dichlorophenylthio)picolinonitrile

HRID 1048769Notes

Reaction equation

HRID 1048769 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([S:10][C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]([N+:19]([O-])=O)=[CH:13][CH:12]=2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.C(OCC)(=O)C.O>CO.[Fe]>[NH2:19][C:14]1[C:15]([C:17]#[N:18])=[N:16][C:11]([S:10][C:5]2[CH:4]=[C:3]([Cl:2])[CH:8]=[C:7]([Cl:9])[CH:6]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 68276433HCID 68276433, compound

Product 1

HCID 682765423-Amino-6-(3,5-dichlorophenylthio)picolinonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

10 ml of concentrated HCl is added to a solution of 6-(3,5-dichlorophenylthio)-3-nitropicolinonitrile (3.4 g, 0.01 mol) in 50 ml of methanol under stirring. The reaction medium is refluxed, added together with 1.68 g (0.03 mol) of iron and stirred for 10 minutes. After returning to room temperature, the reaction mixture is added together with 100 ml of ethyl acetate and 50 ml of water. The pH is adjusted to 10 using 30% soda solution and the organic phase is extracted and then dried on anhydrous sodium sulfate before being concentrated. The residue is purified by silica gel chromatography (ethyl acetate/petroleum ether) to yield, after concentration of the fractions, 2.82 g (91%) of a yellow solid.

Workup

  1. temperatureThe reaction medium is refluxed
  2. stirringstirred for 10 minutes
  3. customAfter returning to room temperature
  4. extractionthe organic phase is extracted
  5. dry with materialdried on anhydrous sodium sulfate
  6. concentrationbefore being concentrated
  7. customThe residue is purified by silica gel chromatography (ethyl acetate/petroleum ether)
  8. customto yield

Sources & evidence

ORD record
ord-d577d3c82a67437a95d2161b3e28fc23
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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