2,4-Dimethoxybenzylamine → 2-[(2,4-Dimethoxyphenyl)methyl]-6-nitroisoquinolin-1(2H)-imine

HRID 2104966Notes

Reaction equation

HRID 2104966 reaction equation
C[N:2]([CH3:16])/[CH:3]=[CH:4]/[C:5]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[O:17]([C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:20]=1CN)[CH3:18]>CN1C(=O)N(C)CCC1>[CH3:18][O:17][C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:20]=1[CH2:16][N:2]1[CH:3]=[CH:4][C:5]2[C:6](=[CH:9][CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=2)[C:7]1=[NH:8]

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 20801671(E)-2-(2-(dimethylamino)vinyl)-4-nitrobenzonitrile

Product 1

HCID 208016702-[(2,4-Dimethoxyphenyl)methyl]-6-nitroisoquinolin-1(2H)-imine

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

(E)-2-(2-(Dimethylamino)vinyl)-4-nitrobenzonitrile (4.6 g, 21.2 mmol) and 2,4-dimethoxylbenzylamine (4.0 mL, 1.25 equiv) in DMPU (10 mL) were heated at 140° C. for 3 h. The solvent was removed by vacuum distillation and residue was treated with hexanes/ethyl acetate (1:1). The solid was collected by filtration and washed with hexane to give 2-(2,4-dimethoxybenzyl)-6-nitroisoquinolin-1 (2H)-imine (4.6 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.72 (s, 3 H) 3.81 (s, 3 H) 4.96 (s, 1 H) 6.28 (d, J=6.59 Hz, 1 H) 6.46 (d, J=7.47 Hz, 1 H) 6.58 (d, J=1.76 Hz, 1 H) 7.03 (d, J=8.79 Hz, 1 H) 7.27 (d, J=6.15 Hz, 1 H) 8.02 (dd, J=9.01, 2.42 Hz, 1 H) 8.31 (d, J=2.20 Hz, 1 H) 8.43 (d, J=8.35 Hz, 1 H).

Workup

  1. customThe solvent was removed by vacuum distillation and residue
  2. additionwas treated with hexanes/ethyl acetate (1:1)
  3. filtrationThe solid was collected by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-6c3aeeb3218a45929bd63167e97003f8
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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