1,2-diethyl-3-nitrobenzene → 3,4-Diethylaniline

HRID 1781043Notes

Reaction equation

HRID 1781043 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH2:12][CH3:13])[CH3:2].[CH2:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:17]=1[CH2:25][CH3:26])[CH3:15]>C(OCC)(=O)C>[CH2:12]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])[NH2:9])[CH3:13].[CH2:25]([C:17]1[C:16]([CH2:14][CH3:15])=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:22])[CH3:26]

Participants

5

Reactant 2

HCID 2985131,2-diethyl-3-nitrobenzeneHCID 145959441,2-Diethyl-4-nitrobenzene

Product 2

HCID 18362470HCID 18362470, compoundYield 19%HCID 223389503,4-DiethylanilineYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,2-diethyl-4-nitrobenzene (16) and 1,2-diethyl-3-nitrobenzene (17) (1.4 g, 7.82 mmol) was dissolved in ethyl acetate (20 mL). To this solution was added 10% Pd--C (350 mg, 20%; Aldrich). The mixture was agitated at room temperature under a pressure of 35 psi (H2) for 10 h. The catalyst was removed through a column of Celite (5 g) and washed with ethyl acetate (3×15 mL). The filtrates were combined and evaporated in vacuo to give a residue, which was separated by preparative TLC (Hexanes:EtOAc=8:2), giving 3,4-diethylaniline (19) (0.822 g, 71%) as a pale yellow oil (Rf =0.7) and 2,3-diethylaniline (20) (0.219 g, 19%) as a brown oil (Rf =0.6). 1H NMR (CDCl3, 300 MHz): δ(19): 1.184 (t, 6H, J=7 Hz), 2.573 (q, 4H, J=7 Hz), 3.456 (br, s, 2H) 6.513 (m, 2H), 6.970 (d, 1H, J=7.8 Hz). (20): 1.215 (t, 6H, J=7 Hz), 2.617 (q, 4H, J=7 Hz), 6.570 (d, 1H, J=7.5 Hz), 6.650 (d, 1H, J=7.5 Hz), 6.973 (m, 1H).

Workup

  1. customThe catalyst was removed through a column of Celite (5 g)
  2. washwashed with ethyl acetate (3×15 mL)
  3. customevaporated in vacuo
  4. customto give a residue, which
  5. customwas separated by preparative TLC (Hexanes:EtOAc=8:2)

Sources & evidence

ORD record
ord-b8d301c6f54d46f7a3a3c206fb56c3c7
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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