Nitric Acid → HCID 19018660, compound
Reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH2:9][CH2:8][CH2:7][N:6]3[C:5]=1[CH3:16].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[Br:1][CH2:2][CH2:3][C:4]1[C:14]2=[C:15]3[C:10](=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[CH:13]2)[CH2:9][CH2:8][CH2:7][N:6]3[C:5]=1[CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5 g 1-(2-bromoethyl)-2-methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline were added to 10 ml of concentrated sulfuric acid cooled to 0° C. The reaction mixture was kept at a temperature of about 0° C., and a mixture of 1.15 ml of concentrated sulfuric acid and 0.84 ml of nitric acid was added dropwise as a nitrating agent. The reaction mixture was kept for a further hour at 0° C. and one more hour at room temperature. To work up the reaction mixture it was poured onto 30 g of ice and extracted with dichloromethane. The organic phase was dried and concentrated. The residue which remained was heated in 10 of ethanol, and the resulting yellowish precipitate was filtered out. 2.26 g of 1-(2-bromoethyl)-2-methyl-8-nitro-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline were obtained as an ochre-colored powder.
Workup
- customwas kept at a temperature of about 0° C.
- additionwas added dropwise as a nitrating agent
- waitThe reaction mixture was kept for a further hour at 0° C.
- customat room temperature
- extractionextracted with dichloromethane
- customThe organic phase was dried
- concentrationconcentrated
- temperatureThe residue which remained was heated in 10 of ethanol
- filtrationthe resulting yellowish precipitate was filtered out
Sources & evidence
- ORD record
- ord-4e2764b6d64646808c80005a194a6f2a
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05324725
Reaction notes
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