2-Isopropylaniline → 5-Nitro-2-(propan-2-yl)aniline

HRID 1915451Notes

Reaction equation

HRID 1915451 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[N+:11]([O-])([O-:13])=[O:12].[K+].[OH-].[Na+]>OS(O)(=O)=O>[CH:1]([C:4]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 125612-IsopropylanilineHCID 14798Sodium HydroxideHCID 24434Potassium Nitrate

Product 1

HCID 189801085-Nitro-2-(propan-2-yl)anilineYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

2-Isopropylaniline (13.5 g, 99.85 mmol) was added portionwise to conc. H2SO4 (100 mL) to generate a yellow homogeneous solution. The solution was then cooled to 0° C. and KNO3 (15.2 g, 150.3 mmol) was added portionwise maintaining the internal temperature below 5° C. The reaction was stirred for 2 h and then poured on ice water, then basified with 10% NaOH solution. The aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and concentrated to obtain 2-isopropyl-5-nitroaniline (14.9 g, 83%). 1H NMR (400 MHz, CDCl3) δ 7.60 (dd, J=8.4, 2.2 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 7.27-7.21 (m, 1H), 3.96 (s, 2H), 2.98-2.79 (m, 1H), 1.29 (d, J=6.8 Hz, 6H).

Workup

  1. temperaturemaintaining the internal temperature below 5° C
  2. additionpoured on ice water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5b09b0fd34c4bab9208e0f8e2d1550e
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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