1-[2-(4,5-Dimethoxy-2-nitro-phenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane → 1-[2-(2-Amino-4,5-dimethoxyphenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

HRID 1380875Notes

Reaction equation

HRID 1380875 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:33])[CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)=[O:13])=[C:5]([N+:34]([O-])=O)[CH:4]=1>CO.[Pd]>[NH2:34][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][C:6]=1[CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:33])[CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[CH:25]=2)[CH2:20]1)=[O:13]

Participants

4

Reactant 1

HCID 233245891-[2-(4,5-Dimethoxy-2-nitro-phenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Product 1

HCID 233246051-[2-(2-Amino-4,5-dimethoxyphenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Here, 1-[2-(4,5-dimethoxy-2-nitro-phenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2 yl)-amino]-propane (8.5 g, 0.017 mol) is dissolved in methanol (100 ml), mixed with 10% palladium on charcoal (9.8 g) and hydrogenated for one hour at 20° C. under hydrogen pressure (5 bar). The catalyst is filtered off and the filtrate is concentrated by rotary evaporation. Yield: 7.8 g. Rf value: 0.2 (alumina, eluant: 98 parts by volume of methylene chloride+2 parts by volume of ethanol).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated by rotary evaporation

Sources & evidence

ORD record
ord-d83e3e88008b4104838a43aa4eaec5d9
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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