2-Methyl-4-methoxyaniline → 6-Chloro-N-(4-methoxy-2-methyl-phenyl)-nicotinamide

HRID 2190529Notes

Reaction equation

HRID 2190529 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[CH:4]=1.[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][N:13]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:10])=[O:17])=[CH:14][N:13]=1

Participants

4

Reactant 3

HCID 76102-Methyl-4-methoxyanilineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 98568436-Chloro-N-(4-methoxy-2-methyl-phenyl)-nicotinamide

Procedure

6-Chloro-N-(4-methoxy-2-methyl-phenyl)-nicotinamide was prepared from 4-methoxy-2-methyl 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 C14H13N2O2Cl [M+H]+: 277.0739. Found: 277.0738.

Workup

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

Sources & evidence

ORD record
ord-ad92a06b152e4e96acd6141cca275a71
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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