Iodoethane → 3-Quinolinamine, 4-(ethylthio)-

HRID 1649729Notes

Reaction equation

HRID 1649729 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:13](I)[CH3:14]>[OH-].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[S:12][CH2:13][CH3:14])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 1785079903-Aminoquinoline-4-thiol

Product 1

HCID 101304463-Quinolinamine, 4-(ethylthio)-Yield 85%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 656671Sodium PyrosulfiteSolvent

Conditions

Temperature
60 °C

Procedure

17.62 g (0.1 mole) of 3-amino-4-quinoline-thiol are dissolved in 50 ml of a 2 molar sodium hydroxide solution whereupon some sodium pyrosulfite crystals are added to the solution. At a temperature below 60° C. 22 g (0.14 mole) of ethyl iodide are added dropwise. The reaction mixture is stirred at 60° C., the product is extracted with chloroform, clarified with activated charcoal and evaporated. Thus 17.3 g of 3-amino-4-ethylthio-quinoline are obtained, yield 85%, b. p.: 147° C./26.6 N.m-2.

Workup

  1. additionare added to the solution
  2. customAt a temperature below 60° C
  3. extractionthe product is extracted with chloroform
  4. customevaporated

Sources & evidence

ORD record
ord-a29e0befb1ed4411892a101993c34749
Source dataset
uspto-grants-1990_05
Patent number
US04921861

Reaction notes

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