Nitric Acid → 2-Chloro-6-methyl-5-nitroquinoline

HRID 1444514Notes

Reaction equation

HRID 1444514 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[C:8]=2[N+:13]([O-:15])=[O:14])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 779742-Chloro-6-methylquinoline

Product 1

HCID 179891062-Chloro-6-methyl-5-nitroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.12 g of 2-chloro-6-methylquinoline (J. Med. Chem. 1992, pp. 2761-2768) is added at 0° C. to a solution that consists of 15 ml of 100% nitric acid and 2 ml of 96% sulfuric acid. After 4 hours at 0° C., it is added to water, and the product is filtered off. 4.66 g of 2-chloro-6-methyl-5-nitroquinoline is obtained as a beige solid. The latter is reacted for 80 hours at 100° C. in 46 ml of glacial acetic acid and 26 ml of water. The thus obtained 6-methyl-5-nitroquinolin-2(1H)-one is filtered off from the reaction solution. The 3.45 g of product that is obtained is reacted with hydrogen under normal pressure in methanol on palladium on activated carbon to form aniline. 2.89 g of the title compound is obtained as a beige solid.

Workup

  1. addition2761-2768) is added at 0° C. to a solution that
  2. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-3b4dc2dd7212468f88a211723ca04bcb
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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