3,5-Dimethoxyaniline → 6-chloro-N-(3,5-dimethoxyphenyl)pyridine-3-carboxamide

HRID 2190528Notes

Reaction equation

HRID 2190528 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][N:14]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:6][C:5]2[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:18])=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 663013,5-DimethoxyanilineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 21016456-chloro-N-(3,5-dimethoxyphenyl)pyridine-3-carboxamide

Procedure

6-Chloro-N-(3,5-dimethoxy-phenyl)-nicotinamide was prepared from 3,5-dimethoxy 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 C14H13N2O3Cl [M+H]+: 293.0688. Found: 293.0687.

Workup

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

Sources & evidence

ORD record
ord-73a9d87f941643b6b4ece9284af1e702
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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