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

HRID 2088468Notes

Reaction equation

HRID 2088468 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:17])[CH:13]=2)[N:8]=1.[N+:18]([O-])([OH:20])=[O:19]>>[Cl:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:17])[C:13]=2[N+:18]([O-:20])=[O:19])[N:8]=1

Participants

4

Reactant 3

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

Product 1

HCID 179891062-Chloro-6-methyl-5-nitroquinolineYield 98%

Conditions

Temperature
100 °C

Procedure

Sulfuric acid(7.2 mL) was added to 2-chloro-6-methyl-quinoline (1.15 g, 6.5 mmol). To the resulting solution was added nitric acid(3.1 mL), and the mixture was heated at 100° C. for 20 minutes. After cooling, the mixture was poured into ice-water. The resulting yellow solid was collected by filtration and dried under vacuum to give 2-chloro-6-methyl-5-nitro-quinoline (1.42 g, 98%).

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting yellow solid was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-60089826bc0a475aa0b871e4fb142d9b
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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