1,2,3,4-Tetrahydroquinoline → 1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

Participants

Role	Name	HCID	Charge
Reactant	1,2,3,4-Tetrahydroquinoline	HCID 69460	—
Reactant	4-Bromo-1-fluoro-2-nitrobenzene	HCID 2736328	—
Reactant	N-[2-(2,3-dihydro-1H-indol-1-yl)-5-fluorophenyl]-4-methyl-1-piperazine carboxamide maleate	HCID 70406853	—
Product	1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline	HCID 13812927	—
Product	5-Bromo-2-[3,4-dihydro-1(2H)-quinolinyl]aniline	HCID 13812931	—
Product	10-bromo-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine	HCID 13812943	—

Reaction Steps

Starting with 1,2,3,4-tetrahydroquinoline and 5-bromo-2-fluoronitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-bromophenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-bromophenyl)-1,2,3,4-tetrahydroquinolin-1-yl}]-4-methyl-1-piperazine carboxamide, and 10-bromo-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04723003
Source dataset	uspto-grants-1988_02
ORD ID	ord-f25e2397d0e44ac98f1fbbc579c59523
Source note	uspto-grants-1988_02