Nitric Acid → 8-Chloro-2-methyl-5-nitroquinoline

HRID 26363

Reaction equation

HRID 26363 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[N+:13]([O-])([OH:15])=[O:14].[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 2211138-Chloro-2-methylquinoline

Product 1

HCID 177506238-Chloro-2-methyl-5-nitroquinolineYield 96.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

53.3 g (0.3 mole) of the resulting 8-chloroquinaldine was dissolved in 180.2 g of 98% sulfuric acid, and at 40° C., 40.2 g of nitric acid (specific gravity 1.50) was added dropwise over the course of 1 hour, followed by further reaction for 30 minutes. The reaction mixture was poured into ice water, and neutralized with an aqueous solution of sodium hydroxide. The product precipitated was collected by filtration, washed with water, and dried to afford 64.1 g (0.29 mole) of 8-chloro-5-nitroquinaldine.

Workup

  1. customfollowed by further reaction for 30 minutes
  2. customThe product precipitated
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-20462d786d2d4e94adfd61fbc12d4b76
Source dataset
uspto-grants-1979_04
Patent number
US04150025

Linked notes

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