3-Methoxyaniline → 6-Chloro-N-(3-methoxyphenyl)nicotinamide

HRID 2190525Notes

Reaction equation

HRID 2190525 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[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:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:16])=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 108243-MethoxyanilineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 184194246-Chloro-N-(3-methoxyphenyl)nicotinamide

Procedure

6-Chloro-N-(3-methoxy-phenyl)-nicotinamide was prepared from 3-methoxyaniline 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 small volume of CH2Cl2 with hexanes. HRMS m/z calcd for C13H11N2OCl [M+H]+: 263.0582. Found: 263.0581.

Workup

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

Sources & evidence

ORD record
ord-e6389d0b4a3b438d9d5c8e3a8b6a3984
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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