3,4-Dimethylaniline → 6-chloro-N-(3,4-dimethylphenyl)pyridine-3-carboxamide

HRID 2190532Notes

Reaction equation

HRID 2190532 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][N:12]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([CH3:1])[CH:3]=2)=[O:16])=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 72483,4-DimethylanilineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 47998276-chloro-N-(3,4-dimethylphenyl)pyridine-3-carboxamide

Procedure

6-Chloro-N-(3,4-dimethyl-phenyl)-nicotinamide was prepared from 3,4-dimethyl aniline and 6-chloronicotinoyl chloride following a procedure similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after precipitation out of a small volume of CH2Cl2 with hexanes. HRMS m/z calcd for C14H13N2OCl [M+H]+: 261.0789. Found: 261.0788

Workup

  1. customThe product was isolated
  2. customafter precipitation out of a small volume of CH2Cl2 with hexanes

Sources & evidence

ORD record
ord-02a83e46c856484590c6241839c65e5f
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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