o-Butyl-aniline → (1-{6-[1-(2-Butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine

HRID 1406597Notes

Reaction equation

HRID 1406597 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]([C:12]1[N:17]=[C:16]([C:18](=O)[CH3:19])[CH:15]=[CH:14][CH:13]=1)[CH3:11].[CH2:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31])[CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1>[CH2:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:18]([C:16]1[N:17]=[C:12]([C:10](=[N:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH3:11])[CH:13]=[CH:14][CH:15]=1)[CH3:19])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 75909o-Butyl-anilineHCID 220656241-{6-[(1E)-N-(2,6-Dimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Product 1

HCID 86674616(1-{6-[1-(2-Butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-{6-[1-(2,6-Dimethyl-phenylimino)-ethyl]-pyridin-2-yl}ethanone 1 (2.3 g, 0.0088 mol), 1.68 g (0.0244 mol) of 2-n-Butyl-phenylamine 12, 100 g of fresh molecular sieves, and 100 ml of toluene were kept at 100° C. for 3 days under the flow of nitrogen. The solvent was removed in a rotary evaporator and the residue was recrystallized from 5 ml of ethanol. The yield of (1-{6-[1-(2-n-butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine 11 was 2.60 g (76%) as a yellow solid. 13C NMR (500 MHz, CD2Cl2, TMS (selected signals)): δ 166.8 (C═N), 166.1 (C═N).

Workup

  1. customThe solvent was removed in a rotary evaporator
  2. customthe residue was recrystallized from 5 ml of ethanol

Sources & evidence

ORD record
ord-9830a7de995e4cbeb2d685c30dc5545f
Source dataset
uspto-grants-2014_12
Patent number
US08916664B2

Reaction notes

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