Sodium Hydroxide → 2,6-Diaminobenzonitrile

HRID 1704270Notes

Reaction equation

HRID 1704270 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:5]=1[C:6]#[N:7])([O-])=O.[OH-].[Na+]>Cl.O>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 520718Dinitrobenzonitrile

Product 1

HCID 124029832,6-DiaminobenzonitrileYield 60.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

2,6-Dinitrobenzonitrile (10.0 grams) is added in portions to a stirred solution of stannous chloride (82.5 grams) in concentrated HCl (230 ml.) at room temperature. Stirring is continued at room temperature for two and one-half hours, then the reaction mixture is cooled to 0° and made strongly basic with 50% NaOH. The reaction mixture is diluted with water (1 l.) and extracted four times with methylenechloride (200 ml.). The combined extracts are washed once with water (200 ml.), dried over sodium sulfate, then taken to dryness under reduced pressure. Recrystallization of the crude solid (4.6 grams) from benzene-Skellysolve "B" gives the product (4.15 grams) melting at 91°-92°.

Workup

  1. customis continued at room temperature for two and one-half hours
  2. temperaturethe reaction mixture is cooled to 0°
  3. extractionextracted four times with methylenechloride (200 ml.)
  4. washThe combined extracts are washed once with water (200 ml.)
  5. dry with materialdried over sodium sulfate
  6. customRecrystallization of the crude solid (4.6 grams) from benzene-Skellysolve "B"

Sources & evidence

ORD record
ord-e8125e59d13b4c0990b44dcedef162d4
Source dataset
uspto-grants-1978_11
Patent number
US04126617

Reaction notes

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