2-Isopropylaniline → (2-Isopropyl-6-methyl-phenyl)-(1-{6-[1-(2-isopropyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-amine

HRID 707732Notes

Reaction equation

HRID 707732 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]=[C:12]([C:14]1[N:19]=[C:18]([C:20](=O)[CH3:21])[CH:17]=[CH:16][CH:15]=1)[CH3:13])([CH3:3])[CH3:2].[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]=[C:12]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([C:20](=[N:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:23]([CH3:25])[CH3:24])[CH3:21])[N:19]=1)[CH3:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 125612-IsopropylanilineHCID 866742401-{6-[1-(2-Isopropyl-6-methyl-phenylimino)-ethyl]-pyridin-2-yl}-ethanone

Product 1

HCID 86674241(2-Isopropyl-6-methyl-phenyl)-(1-{6-[1-(2-isopropyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.0 g (0.0135 mol) of 1-{6-[1-(2-isopropyl-6-methyl-phenylimino)-ethyl]-pyridin-2-yl}-ethanone 15, 2.76 g (0.0204 mol) of 2-Isopropyl-phenylamine 9 (4.0 g, 0.0135 mol), 100 g of fresh molecular sieves, and 100 ml of toluene were kept at 100° C. for 3 days under a flow of nitrogen. The solvent was removed in a rotary evaporator and the residue was recrystallized from 10 ml of ethanol. The yield of (2-Isopropyl-6-methyl-phenyl)-(1-{6-[1-(2-isopropyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-amine 16 was 4.83 g (87%) as a yellow solid. 13C NMR (500 MHz, CD2Cl2, TMS (selected signals)), δ 166.9 (C═N), 166.2 (C═N).

Workup

  1. customThe solvent was removed in a rotary evaporator
  2. customthe residue was recrystallized from 10 ml of ethanol

Sources & evidence

ORD record
ord-41238e8561b74692a3f626a5eddac5e4
Source dataset
uspto-grants-2015_11
Patent number
US09175104B2

Reaction notes

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