Nitric Acid → 6-(2,6-Difluoro-3-nitrophenyl)-quinoline

HRID 980199Notes

Reaction equation

HRID 980199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2.[N+:19]([O-])([OH:21])=[O:20]>OS(O)(=O)=O>[F:1][C:2]1[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 137730476-(2,6-Difluorophenyl)-quinoline

Product 1

HCID 137730486-(2,6-Difluoro-3-nitrophenyl)-quinolineYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The title compound was prepared by the method of Example 1B. A 5.00 g sample (70% yield) was made from 6-(2,6-difluorophenyl)-quinoline (6.02 g, 25 mmoles) and 50 ml of concentrated H2SO4 and 1.5 ml of concentrated HNO3. The product was isolated as an off white solid of m.p. 152°-153° C. NMR (DMSO-d6, 250 MHz): 9.05 (d of d, 1H), 8.50 (d, J=5 Hz, 1H), 8.40 (sextet, 1H), 8.24 (s, 1H), 8.20 (d, J=5.0 Hz, 1H), 7.87 (d, J=5.0 Hz, 1H), 7.60 (m, 2H).

Workup

  1. customThe product was isolated as an off white solid of m.p. 152°-153° C

Sources & evidence

ORD record
ord-5c679352fa8348a883fa221a7298b8cc
Source dataset
uspto-grants-1987_01
Patent number
US04636506

Reaction notes

Loading…