Hydrochloric Acid → 5,6-Dichloro-2-methylquinoline

HRID 1649428Notes

Reaction equation

HRID 1649428 reaction equation
N[C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.N([O-])=O.[Na+].[OH-].[Na+].[ClH:20]>O>[Cl:20][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 155717736-Chloro-2-methylquinolin-5-amineHCID 23668193Sodium Nitrite

Product 1

HCID 155717745,6-Dichloro-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Amino-6-chloroquinaldine (4 g) was dissolved in 40 ml of concentrated hydrochloric acid and the resulting solution was cooled with ice. Then, a solution of 2.1 g of sodium nitrite dissolved in 5 ml of water was added thereto dropwise while ice-cooling. After continuing the reaction at the same temperature as above, the reaction mixture was added to a solution of 7 g of cuprous chloride dissolved in 15 ml of concentrated hydrochloric acid and the resulting mixture was allowed to react on a water bath at a temperature of 50° C. for 1 hour, during which time vigorous formation of nitrogen gas was observed. Subsequently, the reaction mixture was cooled, rendered alkaline with 30% sodium hydroxide, and filtered and extracted using 300 ml of chloroform and Celite (diatomaceous earth). After drying over anhydrous sodium sulfate the chloroform fraction was concentrated and recrystallized from a mixture of isopropanol and water to give 3.5 g of 5,6-dichloroquinaldine as white needles having a melting point of 84° to 85° C.

Workup

  1. temperaturethe resulting solution was cooled with ice
  2. additionwas added
  3. temperaturedropwise while ice-cooling
  4. customthe reaction at the same temperature as above, the reaction mixture
  5. customto react on a water bath at a temperature of 50° C. for 1 hour, during which time vigorous formation of nitrogen gas
  6. temperatureSubsequently, the reaction mixture was cooled
  7. filtrationfiltered
  8. extractionextracted
  9. dry with materialAfter drying over anhydrous sodium sulfate the chloroform fraction
  10. concentrationwas concentrated
  11. customrecrystallized from a mixture of isopropanol and water

Sources & evidence

ORD record
ord-8d18afc6aa8545bf96cf7d5a2dcd880b
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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