Hydrochloric Acid → 2,5-Diaminobenzonitrile

HRID 1834040Notes

Reaction equation

HRID 1834040 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[C:9]([C:10]#[N:11])[C:8]([NH2:13])=[CH:7][CH:6]=1)([O-])=O.[OH-].[Na+]>O>[NH2:13][C:8]1[CH:7]=[CH:6][C:5]([NH2:2])=[CH:12][C:9]=1[C:10]#[N:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 285322-Amino-5-nitrobenzonitrile

Product 1

HCID 136473082,5-DiaminobenzonitrileYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 80 grams (0.356 mole) of stannous chloride dihydrate in 200 ml. of concentrated hydrochloric acid is added in portions over the course of about 5 minutes, 16.314 grams (0.1 mole) of 5-nitroanthranilonitrile. Water cooling is used and the internal temperature rises to about 50°. Stirring is continued for 4 hours and the mixture is allowed to stand overnight. The reaction mixture is cooled to 5° in an ice-bath and a cold 50% solution of sodium hydroxide added until the mixture is strongly basic. The mixture is extracted with methylene chloride. The methylene chloride extracts are washed with water and the solvent removed by distillation. There is obtained 11.51 grams (86.5%) of material melting at 85°-87°. Recrystallization from benzene-skellysolve B gives material melting at 86°-7°. The infrared spectrum is in agreement.

Workup

  1. customrises to about 50°
  2. waitto stand overnight
  3. temperatureThe reaction mixture is cooled to 5° in an ice-bath
  4. extractionThe mixture is extracted with methylene chloride
  5. washThe methylene chloride extracts are washed with water
  6. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-ce89a7d2d894405b94a037fe3fea25dc
Source dataset
uspto-grants-1978_01
Patent number
US04067995

Reaction notes

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