Water → 3,4-Diaminobenzonitrile

HRID 2080791Notes

Reaction equation

HRID 2080791 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:7]#[N:8])([O-])=O.[BH4-].[Na+].O.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:7]#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5959014-Amino-3-nitrobenzonitrileHCID 4311764Sodium borohydride

Product 1

HCID 7372853,4-DiaminobenzonitrileYield 45.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

3-Nitro-4-aminobenzonitrile (3.00 g) was dissolved in ethanol (300 ml) and added with stannous chloride dihydrate (20.7 g) and the whole was heated to 60° C. Sodium borohydride (348 mg) was gradually added thereto and the whole was stirred overnight at 60° C. After completion of the reaction, the resultant was added with water (300 ml) and neutralized with a 5 mol/l sodium hydroxide aqueous solution. After ethanol was distilled off under reduced pressure, the aqueous layer was added with ethyl acetate for extraction. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was recrystallized, thereby obtaining the subject compound (1.11 g) as a brown crystal.

Workup

  1. customAfter completion of the reaction
  2. distillationAfter ethanol was distilled off under reduced pressure
  3. additionthe aqueous layer was added with ethyl acetate for extraction
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized

Sources & evidence

ORD record
ord-9cce3c04b41d4582a0401330f082c2fd
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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