Nitric Acid → 6-Nitroquinolin-2(1H)-one

HRID 373783Notes

Reaction equation

HRID 373783 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.O>S(=O)(=O)(O)O>[N+:1]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:5])[CH:15]=[CH:14]2)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 178515546HCID 178515546, compound

Product 1

HCID 8999326-Nitroquinolin-2(1H)-oneYield 67%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (70%), 2.3 mL, was added dropwise to a stirred mixture of 2-hydroxyquinoline (available commercially or by one of the methods described in Beilstein 21, 77) 3.5 g (0.024 mole), in 20 mL of concentrated sulfuric acid at 0° C. The reaction mixture was stirred for 2 hours at room temperature and then poured into ice and water. The resulting solid was collected by filtration, washed with cold water and then digested twice with hot methanol to yield 3 g (67%) of 6-nitrocarbostyril as crystals; m.p. 280°-282° C.

Workup

  1. customat 0° C
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with cold water

Sources & evidence

ORD record
ord-2412aafaf56549e5bdaf68fac399747d
Source dataset
uspto-grants-1992_11
Patent number
US05166160

Reaction notes

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