4-Aminophenol → 4-Chloro-N-methylpicolinamide

HRID 78383

Reaction equation

HRID 78383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH3:11])=[O:9])[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH3:11])=[O:9])[CH:3]=1.[CH3:11][NH:10][C:8]([C:4]1[CH:3]=[C:2]([O:19][C:16]2[CH:17]=[CH:18][C:13]([NH2:12])=[CH:14][CH:15]=2)[CH:7]=[CH:6][N:5]=1)=[O:9]

Participants

5

Reactant 2

HCID 4034-AminophenolHCID 14768144-Chloro-N-methylpicolinamide

Product 2

HCID 14768144-Chloro-N-methylpicolinamideHCID 166551294-(4-Aminophenoxy)-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Entry 103: 4-Chloro-N-methyl-2-pyridinecarboxamide was synthesized according to Method A2, Step 3b. 4-Chloro-N-methyl-2-pyridinecarboxamide was reacted with 4-aminophenol according to Method A2, Step 4 using DMAC in place of DMF to give 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline. According to Method C2b, reaction of 3-amino-2-methoxyquinoline with CDI followed by 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline afforded bis(4-(2-(N-methylcarbamoyl)-4-pyridlyoxy)phenyl)urea.

Sources & evidence

ORD record
ord-2744b4db45e24ad68eba16d25b07aaea
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Linked notes

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