1,8-Diazabicyclo(5.4.0)undec-7-ene → 7,8-dihydro-3-nitro-6H-cyclopenta[g]quinoline

HRID 36930Notes

Reaction equation

ClC1C=CC=CC=1[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][C:7]=1[NH:15][CH:16]=[CH:17][N+:18]([O-:20])=[O:19])=O.C1CCN2C(=NCCC2)CC1>C1C=CC=CC=1>[N+:18]([C:17]1[CH:16]=[N:15][C:7]2[C:6]([CH:4]=1)=[CH:14][C:13]1[CH2:12][CH2:11][CH2:10][C:9]=1[CH:8]=2)([O-:20])=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

6-(2-Chlorobenzoyl)-5-(2-nitroethenylamino)indan (4.8 g) was added in small portions to a solution of DBU (4.8 g) in benzene (50 ml) with heating at 90° C. The mixture was refluxed for 30 minutes and, then, washed with 2N HCl and water and dried (MgSO4). The solvent was then distilled off to give crystals of 4-2-chlorophenyl)-7,8-dihydro-3-nitro-6H -cyclopenta[g]quinoline. The crystals were collected by filtration and washed with methanol (4.50 g, 99.1%). Recrystallization from ethanol gave light brown prisms, mp. 175°-176° C.

Workup

temperatureThe mixture was refluxed for 30 minutes
washwashed with 2N HCl and water
dry with materialdried (MgSO4)
distillationThe solvent was then distilled off

Sources & evidence

ORD record: ord-f4f7f8af08964c71ac06daedd7fb8b15
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05418239

Reaction notes

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