N,N-Dimethyl-1,3-propanediamine → N-(3-(Dimethylamino)propyl)-3-hydroxynaphthalene-2-carboxamide

HRID 1284453Notes

Reaction equation

HRID 1284453 reaction equation
[OH:1][C:2]1[C:11]([C:12]([O:14]C)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[CH3:16][N:17]([CH2:19][CH2:20][CH2:21][NH2:22])[CH3:18]>C1(C)C=CC=CC=1>[CH3:16][N:17]([CH3:18])[CH2:19][CH2:20][CH2:21][NH:22][C:12]([C:11]1[C:2]([OH:1])=[CH:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=1)=[O:14]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 70163Methyl 3-hydroxy-2-naphthoate

Product 1

HCID 88252N-(3-(Dimethylamino)propyl)-3-hydroxynaphthalene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The coupling component used in this Example was obtained by reacting methyl 2-hydroxy-3-naphthoate with dimethylamino propylamine in toluene to obtain N,N-dimethyl-N-3-(3-hydroxy-2-naphthamido)propylamine, and converting the amide compound isolated by filtration, with dimethylsufuric acid in methanol, to a quaternary ammonium form. Further, the amide compound may also be readily prepared via 2-hydroxy-3-napthoic acid chloride.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-54a7243b2ae04828afc4751d2c81bd30
Source dataset
uspto-grants-1986_01
Patent number
US04563409

Reaction notes

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