Potassium Hydroxide → 2-Amino-5-(naphth-2-ylthio)benzonitrile

HRID 1734592Notes

Reaction equation

HRID 1734592 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[OH-].[K+]>COCCOCCOC.Cl>[NH2:1][C:4]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 542131652-Nitro-5-(naphth-2-ylthio)benzonitrile

Product 1

HCID 8252772-Amino-5-(naphth-2-ylthio)benzonitrileYield 103.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8150DiglymeSolvent

Procedure

A stirred solution of 13.0 grams (0.042 mole) of 2-nitro-5-(naphth-2-ylthio)benzonitrile in 200 mL of 2-methoxyethyl ether was cooled to 0° C., and a solution of 30.3 grams (0.134 mole) of stannous chloride dihydrate in 91 mL of concentrated hydrochloric acid was added. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature, where it was stirred during a 2 hour period. After this time, the reaction mixture was poured, with stirring, into a mixture of 260 grams of aqueous 50% potassium hydroxide in 300 grams of ice. An oily material, which dropped out of the solution, ultimately solidified. The solid was collected by filtration and was washed with water. The solid was dissolved in methylene chloride and was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 12.0 grams of 2-amino-5-(naphth-2-ylthio)benzonitrile. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. additionAfter this time, the reaction mixture was poured
  3. additionAn oily material, which dropped out of the solution
  4. filtrationThe solid was collected by filtration
  5. washwas washed with water
  6. dissolutionThe solid was dissolved in methylene chloride
  7. dry with materialwas dried with magnesium sulfate
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ad89c89a65dc433ab609a58284fbc057
Source dataset
uspto-grants-1996_07
Patent number
US05534518

Reaction notes

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