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Ethanol → 5-Bromo-2-[3,4-dihydro-1(2H)-quinolinyl]aniline

HRID 4044
Notes
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Reaction equation

HRID 4044 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[C:4]([N+:18]([O-])=O)[CH:3]=1.C(O)C>C1C=CC=CC=1.[Pt]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[C:4]([NH2:18])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 702EthanolHCID 138129271-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 138129315-Bromo-2-[3,4-dihydro-1(2H)-quinolinyl]anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 241BenzeneSolvent

Procedure

1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (11.6 g, 0.035 mole) was dissolved in benzene (125 ml), and ethanol added (75 ml), followed by 1% platinum-on-charcoal (0.40 g). The mixture was shaken under an initial pressure of 56 psi for 6.5 hours. The mixture was filtered and the filtrate was evaporated at 50° C. under vacuum to provide 10.6 g (100%) of product, as a gum.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated at 50° C. under vacuum

Sources & evidence

ORD record
ord-be31b5d785ad45829427ebbf59eaec37
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04723007

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes