Benzene → 1-(2-Aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline maleate

HRID 4040

Reaction equation

HRID 4040 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)[CH2:7][CH2:6][CH2:5]2.C1C=CC=CC=1.C(O)C.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>CCOCC.[Pt]>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 444266Maleic AcidHCID 138129286-Bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 704069761-(2-Aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline maleateYield 55%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A Parr hydrogenation bottle was charged with 6-bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (16.7 g, 0.050 mole), 1% platinum-on-carbon (1 g), benzene (100 ml) and ethanol (100 ml). The mixture was shaken under an initial hydrogen pressure of 58 psi until uptake ceased. The mixture was then filtered to remove the catalyst and the filtrate was concentrated under vacuum. The residue was taken up in hot ether (150 ml), filtered, and the filtrate was treated with a hot solution of maleic acid (6.4 g, 0.055 mole) in ether (500 ml). The solution was boiled down to about 300 ml and allowed to cool. The supernatant was decanted from an oil, which separated. The supernatant was concentrated and the process was repeated several times to give 11.4 g (55%) of product. Recrystallization from ethyl acetate afforded the analytical sample, mp 113°-116° C.

Workup

  1. filtrationThe mixture was then filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under vacuum
  4. filtrationfiltered
  5. temperatureto cool
  6. customThe supernatant was decanted from an oil, which
  7. customseparated
  8. concentrationThe supernatant was concentrated

Sources & evidence

ORD record
ord-2b04d48d5e5a4e3d9c091e3fa05cb57e
Source dataset
uspto-grants-1988_02
Patent number
US04723007

Linked notes

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