2,N-Dimethylaniline → 4-(2,5-Dichloro-phenoxy)-N-methyl-N-o-tolyl-nicotinamide

HRID 1966987Notes

Reaction equation

HRID 1966987 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]C[CH2:14]1)=[O:12].CNC1C(C)=CC=CC=1>CCCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:3]=1[O:4][C:5]1[C:6]([C:11]([N:13]([CH3:14])[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:16])=[O:12])=[CH:7][N:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 691372,N-DimethylanilineHCID 53311781[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinolin-1-yl)-methanone

Product 1

HCID 461945684-(2,5-Dichloro-phenoxy)-N-methyl-N-o-tolyl-nicotinamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to Example 1, from 4-(2,5-dichloro-phenoxy)-nicotinic acid (Example 1, intermediate) and N-methyl-o-toluidine (commercially available; CAS RN 611-21-2) and using a gradient of n-heptane:ethyl acetate (100:0 to 40:60). The compound was further purified through a second preparative HPLC chromatography (Phenomenex Gemini column) using a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2). White solid (35%). MS (ESI): m/z=387.066 [M+H]+.

Workup

  1. customThe compound was further purified through a second preparative HPLC chromatography (Phenomenex Gemini column)

Sources & evidence

ORD record
ord-a8bdeb3a2c8c4af2b775e4818eb077b7
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

Loading…