P-Anisidine → 6-chloro-N-(4-methoxyphenyl)nicotinamide

HRID 2190524Notes

Reaction equation

HRID 2190524 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[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:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:16])=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 7732P-AnisidineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 14832696-chloro-N-(4-methoxyphenyl)nicotinamide

Procedure

6-Chloro-N-(4-methoxy-phenyl)-nicotinamide was prepared from 4-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: 263.0582.

Workup

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

Sources & evidence

ORD record
ord-42e8933b7a124f34834c3bc5f5fbe5a9
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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