Nitric Acid → 5-Bromo-6-nitro-2-(1-piperazinyl)quinoline

HRID 1492114Notes

Reaction equation

HRID 1492114 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[N:7]2.[N+:18]([O-])([OH:20])=[O:19]>OS(O)(=O)=O.[OH-].[Na+]>[Br:1][C:2]1[C:11]([N+:18]([O-:20])=[O:19])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([N:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)=[N:7]2

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 641346HCID 641346, compound

Product 1

HCID 103149945-Bromo-6-nitro-2-(1-piperazinyl)quinolineYield 70%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a -10° C. solution of 10 (300 mg, 1.03 mmol) in H2SO4 (10 ml) was added dropwise HNO3 (0.25 ml). The mixture was stirred 15 min. at -10° -0° C., poured onto ice, and diluted with 1M NaOH until basic. The mixture was then extracted with CH2Cl2 (3×), and the combined organic layers were dried (MgSO4). Concentration yielded 2a (240 mg, 70%) as a yellowish solid which was utilized in the next step without further purification. (m.p.>230° C., dec. ). 1H NMR d (ppm): 1.79 s (NH), 3.00 dd (CH2), 3.80 dd (CH2), 7.07 d (CH arom), 7.57 d (CH arom), 7.81 d (CH arom), 8.37 d (CH arom).

Workup

  1. additionpoured onto ice
  2. extractionThe mixture was then extracted with CH2Cl2 (3×)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-7d26e40513aa4bb285059cc24c4f58b8
Source dataset
uspto-grants-1994_12
Patent number
US05372813

Reaction notes

Loading…