Benzonitrile, 2,5-dimethyl-4-nitro- → 4-Amino-2,5-dimethylbenzonitrile

HRID 567812Notes

Reaction equation

HRID 567812 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([CH3:13])=[CH:6][C:3]=1[C:4]#[N:5]>C(O)C.[Pd]>[NH2:10][C:8]1[C:7]([CH3:13])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH3:1])[CH:9]=1

Participants

4

Reactant 1

HCID 52273Benzonitrile, 2,5-dimethyl-4-nitro-

Product 1

HCID 184708764-Amino-2,5-dimethylbenzonitrileYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,5-Dimethyl-4-nitrobenzonitrile (500 mg, 2.84 mmol; purchased from Salor) was dissolved in ethanol (20 ml), treated with 10% Pd on carbon catalyst (50 mg) and stirred under a hydrogen atmosphere (10 psi, room temperature, 3 hr). The catalyst was removed by filtration and the solvent evaporated to dryness. The resultant mixture was dissolved in CH2Cl2 and washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2. Solvent was evaporated from the organic layer to give the desired product (brown solid, 350 mg, 84%). 1H NMR (CD3OD) δ 2.10 (s, 3H), 2.30 (s, 3H), 6.60 (s, 1H), 7.20 (s, 1H). LRMS m/z=147.4 (M+1)+. Found C 72.12, H 6.86, N 18.53%; C9H10N2.0.2H2O requires C 72.16, H 7.00, N 18.70%.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated to dryness
  3. dissolutionThe resultant mixture was dissolved in CH2Cl2
  4. washwashed with HCl (2N, 4×15 ml), aqueous layer
  5. additionwas treated with NaHCO3
  6. extractionthen extracted repeatedly with CH2Cl2
  7. customSolvent was evaporated from the organic layer

Sources & evidence

ORD record
ord-915899503f074f13a6d3bb6229d0f59d
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

Loading…