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Title: Method for preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline from 1,2,3,4-tetrahydroquinoline

Abstract

Methods for the efficient preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline include a first method in which the acylation of m-aminophenol obtains a lactam which is reduced to give the desired quinoline and a second method in which tetrahydroquinoline is nitrated and hydrogenated and then hydrolyzed to obtain the desire quinoline. 7-hydroxy-1,2,3,4-tetrahydroquinoline is used in the efficient synthesis of four lasing dyes of the rhodamine class.

Inventors:
 [1];  [2]
  1. Danville, CA
  2. Livermore, CA
Issue Date:
Research Org.:
Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
OSTI Identifier:
869144
Patent Number(s):
5283336
Assignee:
United States of America as represented by United States (Washington, DC)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C - CHEMISTRY C09 - DYES C09B - ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS},
DOE Contract Number:  
W-7405-ENG-48
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
method; preparation; 7-hydroxy-1234-tetrahydroquinoline; 1234-tetrahydroquinoline; methods; efficient; acylation; m-aminophenol; obtains; lactam; reduced; desired; quinoline; tetrahydroquinoline; nitrated; hydrogenated; hydrolyzed; obtain; desire; synthesis; lasing; dyes; rhodamine; lasing dyes; /999/

Citation Formats

Field, George, and Hammond, Peter R. Method for preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline from 1,2,3,4-tetrahydroquinoline. United States: N. p., 1994. Web.
Field, George, & Hammond, Peter R. Method for preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline from 1,2,3,4-tetrahydroquinoline. United States.
Field, George, and Hammond, Peter R. Sat . "Method for preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline from 1,2,3,4-tetrahydroquinoline". United States. https://www.osti.gov/servlets/purl/869144.
@article{osti_869144,
title = {Method for preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline from 1,2,3,4-tetrahydroquinoline},
author = {Field, George and Hammond, Peter R},
abstractNote = {Methods for the efficient preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline include a first method in which the acylation of m-aminophenol obtains a lactam which is reduced to give the desired quinoline and a second method in which tetrahydroquinoline is nitrated and hydrogenated and then hydrolyzed to obtain the desire quinoline. 7-hydroxy-1,2,3,4-tetrahydroquinoline is used in the efficient synthesis of four lasing dyes of the rhodamine class.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1994},
month = {1}
}

Works referenced in this record:

Synthese von Carbostyrilen und Dihydrocarbostyrilen
journal, November 1959


Eine neue Darstellungsweise von Hydro-carbostyril und seinen Abkömmlingen
journal, April 1927


Studies on the Synthetic Analgesics. XVI. Synthesis of 1-(2-tert-Aminoalkyl)-3, 4-dihydrocarbostyrils.
journal, January 1961