Dimethylformamide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid

HRID 968013Notes

Reaction equation

HRID 968013 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1N(C)C.[C:28](=O)([O-])[O-].[K+].[K+].C[N:35]([CH:37]=O)C>[Cu]>[CH2:14]([CH:13]([NH:12][C:7]1[C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:35][C:37]2[C:24]([CH3:20])=[CH:25][C:26]([CH3:28])=[CH:27][C:19]=2[CH3:18])[N:10]=[C:9]([CH3:11])[CH:8]=1)[CH2:16][CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11869N,N,2-TrimethylanilineHCID 248066612-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid

Product 1

HCID 248062594-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

The title compound was prepared by heating 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid and trimethylaniline in the presence of potassium carbonate and copper in DMF. The desired product was isolated by silica gel column chromatography using 5% methanol in chloroform as solvent to give a tan solid, mp. 130-135° C.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-70940a9dab06419bb1d0f36cd76ad076
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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