2,6-Dichloroisonicotinic acid → HCID 86670744, compound

HRID 878121Notes

Reaction equation

HRID 878121 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Cl:26])[N:25]=1)[C:20]([OH:22])=O>CCOC(C)=O>[Cl:26][C:24]1[CH:23]=[C:19]([CH:18]=[C:17]([Cl:16])[N:25]=1)[C:20]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:22]

Participants

4

Reactant 2

HCID 948302,6-Dichloroisonicotinic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 86670744HCID 86670744, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 2,6-dichloro-isonicotinic acid (CAS RN 5398-44-7) after a reaction time of 18 hours. The compound was purified by silica gel chromatography on a 50 g column using a MPLC system eluting with EtOAc (isocratic). The product-containing fractions were pooled and evaporated to give a colorless foam. The foam was dissolved in EtOAc and washed three times with 2M aqueous Na2CO3 solution and brine, dried over MgSO4, filtered and evaporated. Colorless foam (13%). MS (ESI): m/z=372.07 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 50 g column
  2. washeluting with EtOAc (isocratic)
  3. customevaporated
  4. customto give a colorless foam
  5. washwashed three times with 2M aqueous Na2CO3 solution and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a8da973fcf194560a49c7f98696f1087
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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