Nitric Acid → 2-Chloro-5-nitroquinoline

HRID 2054944Notes

Reaction equation

HRID 2054944 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1>>[Cl:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N+:6]([O-:9])=[O:7])[N:12]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 119282-Chloroquinoline

Product 1

HCID 3192512-Chloro-5-nitroquinoline

Procedure

69 ml of 96% sulfuric acid is carefully added in drops to 84 ml of 100% nitric acid. While being cooled with ice, 25 g (152 mmol) of 2-chloroquinoline is added thereto, and the batch is heated for 1 hour to 60° C. After cooling to room temperature, the batch is carefully incorporated into an ice/water mixture. After 15 minutes of stirring, the solid is washed with water and dried in a vacuum at 40° C. Column chromatography on silica gel with hexane-ethyl acetate yields 10.7 g of a white solid.

Workup

  1. additionis added
  2. temperaturethe batch is heated for 1 hour to 60° C
  3. washthe solid is washed with water
  4. customdried in a vacuum at 40° C

Sources & evidence

ORD record
ord-c0ce14f33de34572a92816215f335b6f
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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