N-Ethyl-2-nitroaniline → 1,2-Benzenediamine, N1-ethyl-

HRID 2121919Notes

Reaction equation

HRID 2121919 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-])=O)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])[CH3:2]

Participants

4

Reactant 1

HCID 82354N-Ethyl-2-nitroaniline

Product 1

HCID 902751,2-Benzenediamine, N1-ethyl-Yield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-Ethyl-2-nitroaniline (0.97 g, 5.8 mmol) was dissolved in EtOAc (60 mL) and placed in a closed vessel. 10% Pd/C (0.4 g, 7 mol %) was added and the mixture was hydrogenated under 50 psi H2 for 2 h. The mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield the title product (0.79 g, 99%) as a brown liquid, which was used without further purification. 1H-NMR (CDCl3): δ 6.83 (1H, m), 6.64-6.74 (3H, m), 3.29 (3H, br s), 3.15 (2H, q), 1.30 (3H, t); TLC (2:98 MeOH/DCM Rf 0.24).

Workup

  1. customplaced in a closed vessel
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e6ea41ee9de2443ba983dcfb4babbd99
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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