4-Amino-3-nitrobenzonitrile → 3,4-Diaminobenzonitrile

HRID 1791931Notes

Reaction equation

HRID 1791931 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O>CO.O1CCCC1.[Pd]>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[NH2:1])[C:6]#[N:7]

Participants

5

Reactant 1

HCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 7372853,4-DiaminobenzonitrileYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-3-nitrobenzonitrile (25 g) was dissolved in methanol (200 mL) and tetrahydrofuran (200 mL). The mixture was stirred in the presence of 10% palladium/carbon (3.0 g) under a hydrogen atomosphere (1 atm) for 20 hr. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure to give 3,4-diaminobenzonitrile (20 g) as a charcoal brown solid.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e62a5004f074b199fdeda059775825a
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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