1,2-Benzenedicarbonitrile, 4-nitro- → 1,2-Benzenedicarbonitrile, 4-amino-

HRID 1890405Notes

Reaction equation

HRID 1890405 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

Participants

4

Reactant 1

HCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 925291,2-Benzenedicarbonitrile, 4-amino-Yield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

4-nitrophthalonitrile (3, 60.0 g, 0.346 mol) was dissolved in 190 proof EtOH (528 g) in a pressure reactor to which was added 10% Pd/C (5.59 g) and then heated to 30° C. and pressurized to 60 psi with H2. After 3 hrs, gas consumption ceased. The reaction mixture was purged with N2, filtered through Celite® and concentrated to give 39.5 g (80%) product as a light brown powder. It was used without further purification in the next step. 1H NMR (DMSO-d6) δ: 7.63 (d, J=8.8 Hz, 1H); 7.02 (d, J=2.0 Hz, 1H); 6.87 (dd, J=8.5, 2.0 Hz, 1H); 6.71 (s, 2H). 13C{1H}NMR (DMSO-d6): 153.5, 135.4, 118.0, 117.7, 117.4, 116.9, 116.0, 98.2 ppm. mp 174-176° C.

Workup

  1. customgas consumption
  2. customThe reaction mixture was purged with N2
  3. filtrationfiltered through Celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-754df3329c804848ae79107bf27e9e6d
Source dataset
uspto-grants-2013_08
Patent number
US08507153B2

Reaction notes

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