Acetic Acid → N,N-Dibutyl-4-nitroaniline

HRID 1243149Notes

Reaction equation

HRID 1243149 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:11](=O)[CH2:12][CH2:13][CH3:14].C(O[BH-](O[C:26](=O)[CH3:27])OC(=O)C)(=O)C.[Na+].[C:30](O)(=O)[CH3:31]>ClCCCl>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]([CH2:30][CH2:31][CH2:26][CH3:27])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 74754-NitroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 13795418N,N-Dibutyl-4-nitroanilineYield 44%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-nitroaniline (1.4 g, 10 mmol) in 1,2-dichloroethane (10 ml) at 0° C. was added butyraldehyde (1.8 g, 25 mmol). The reaction mixture was stirred for 0.5 hour, then sodium triacetoxyborohydride (5.3 g, 25 mmol) and acetic acid (1 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Solvent were removed under reduced pressure and the residue purified on column of silica gel to provide the titled 4-nitro-N,N-dibutylaniline (1.1 g, 44%) as a yellow solid. 1HNNMR (CDCl3, 300 MHz), δ ppm 8.10 and 6.58 (d, J=9 Hz, 4H, Ar—H), 3.36 (t, J=9.0 Hz, 4H, 2 NCH2), 1.6 (m, 4H, 2CH2), 1.48 (m, 4H, 2CH2), 0.98 (t, 6H, 2CH3), MS (ESI) (M+1)+ 251.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. customSolvent were removed under reduced pressure
  3. customthe residue purified on column of silica gel

Sources & evidence

ORD record
ord-58509acf5616470692c01a382efea8fe
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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