3-Chloro-5-(trifluoromethoxy)benzoic acid → 3-Chloro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethoxy-benzamide

HRID 878094Notes

Reaction equation

HRID 878094 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]([O:26][C:27]([F:30])([F:29])[F:28])[CH:25]=1)[C:20]([OH:22])=O>CCCCCCC.CCOC(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH: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 177507353-Chloro-5-(trifluoromethoxy)benzoic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 706635663-Chloro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethoxy-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3-chloro-5-(trifluoromethoxy)benzoic acid (CAS RN 158580-93-9) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Yellow solid (31%). MS (ESI): m/z=421.09 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-062ceab46b7f45f783c105bf9c76a613
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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