5,6-Dimethoxy-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine → 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

HRID 1380874Notes

Reaction equation

HRID 1380874 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][C:12]([OH:14])=O)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:37])[CH:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][C:27]([O:35][CH3:36])=[C:28]([O:33][CH3:34])[CH:29]=2)[CH2:24]1.COC1C(OC)=CC=C2C=1CCC(NC)C2>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][C:12]([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:37])[CH:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][C:27]([O:35][CH3:36])=[C:28]([O:33][CH3:34])[CH:29]=3)[CH2:24]2)=[O:14])=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1

Participants

5

Reactant 3

HCID 306585,6-Dimethoxy-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amineHCID 270941(4,5-Dimethoxy-2-nitro-phenyl)-acetic acidHCID 150452791-Amino-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Product 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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound of this paragraph is prepared from 4,5-dimethoxy-2-nitrophenylacetic acid (5.25 g, 0.0217 mol) and of 1-amino-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (6.04 g, 0.0218 mol) analogously to Example R(c). Yield: 8.6 g. Rf value: 0.8 (alumina, eluant: 95 parts by volume of methylene chloride+5 parts by volume of ethanol).

Sources & evidence

ORD record
ord-04e3ede4f1144ba4a8ffc962ce41bf4a
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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