4,5-diethyl-2-nitroaniline → 4,5-Diethylbenzene-1,2-diamine

HRID 1600751Notes

Reaction equation

HRID 1600751 reaction equation
[CH2:1]([C:3]1[C:9]([CH2:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-])=O)[CH:4]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:10]([C:9]1[C:3]([CH2:1][CH3:2])=[CH:4][C:5]([NH2:12])=[C:6]([NH2:7])[CH:8]=1)[CH3:11]

Participants

4

Reactant 1

HCID 2516734,5-diethyl-2-nitroaniline

Product 1

HCID 220965954,5-Diethylbenzene-1,2-diamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4,5-Diethyl-2-nitroaniline (23) (567 mg, 2.92 mmol) was dissolved in ethyl acetate (20 mL). To this solution was added 10% Pd-C (142 mg, 20%; Aldrich). The mixture was agitated at room temperature under a pressure of 35 psi (H2) for 5 h. The catalyst was removed through a column of Celite (5 g) and washed with ethyl acetate (3×20 mL). The filtrates were combined and evaporated in vacuo to give 4,5-diethyl-1,2-diaminobenzene 24 (459 mg, 96%) as a colorless solid; mp 114-116° C. (lit. mp 114-115° C.; Lambooy, J. P., J. Am. Chem. Soc. 71:3756 (1949)); 1H NMR (CDCl3, 300 MHz) δ 1.158 (t, 6H, J=7.5 Hz), 2.498 (q, 4H, J=7.5 Hz), 2.908 (br, s, 4H), 6.555 (s, 2H).

Workup

  1. customThe catalyst was removed through a column of Celite (5 g)
  2. washwashed with ethyl acetate (3×20 mL)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-292cd8891a7f475bbba9ba9e7b23f3bf
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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