Sodium Hydroxide → 6-Chloro-2-methylquinolin-5-amine

HRID 1649427Notes

Reaction equation

HRID 1649427 reaction equation
[N+:1]([C:4]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH3:15])=[N:9]2)([O-])=O.[OH-].[Na+]>Cl>[NH2:1][C:4]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH3:15])=[N:9]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 155717726-Chloro-2-methyl-5-nitroquinoline

Product 1

HCID 155717736-Chloro-2-methylquinolin-5-amineYield 77.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 50 ml of concentrated hydrochloric acid having dissolved therein 25 g of stannous chloride was added 6.7 g of 5-nitro-6-chloroquinaldine and the mixture was allowed to react on a water bath at a temperature of 80° to 90° C. for 30 minutes. The reaction mixture was ice-cooled, rendered alkaline (pH 10) with 30% sodium hydroxide and filtered and extracted with 500 ml of chloroform and Celite (diatomaceous earth). After drying over anhydrous sodium sulfate the chloroform fraction was concentrated and recrystallized from a mixture of benzene and hexane to obtain 4.5 g of 5-amino-6-chloroquinaldine as colorless plates having a melting point of 196° to 197° C.

Workup

  1. customto react on a water bath at a temperature of 80° to 90° C. for 30 minutes
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionextracted with 500 ml of chloroform and Celite (diatomaceous earth)
  5. dry with materialAfter drying over anhydrous sodium sulfate the chloroform fraction
  6. concentrationwas concentrated
  7. customrecrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-34d7129915b048889815a2175c467176
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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