Nitric Acid → 5-Nitro-2-(propan-2-yl)aniline

HRID 2370968Notes

Reaction equation

HRID 2370968 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])([CH3:7])[CH3:6]>S(=O)(=O)(O)O>[CH:5]([C:8]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]=1[NH2:10])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 125612-Isopropylaniline

Product 1

HCID 189801085-Nitro-2-(propan-2-yl)anilineYield 16%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

70% HNO3 (5.1 mL, 84.76 mmol, 1.2 equiv) was added dropwise to a mixture of 2-isopropylaniline (10 mL, 9.55 g, 70.63 mmol, 1 equiv) in 70 mL of conc. sulfuric acid at 0° C. The reaction mixture was stirred at this temperature for 30 minutes and then poured onto ice. The aqueous mixture was extracted with EtOAc (2×150 mL). The organic layers were combined and washed with sat'd NaHCO3. After evaporation, the residue was purified by column chromatography on silica gel using EtOAc/hexanes (3/7) to give 2 g of product (16%) as a dark red oil.

Workup

  1. additionpoured onto ice
  2. extractionThe aqueous mixture was extracted with EtOAc (2×150 mL)
  3. washwashed with sat'd NaHCO3
  4. customAfter evaporation
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a40588f3746c41e49149d8a208ed3d64
Source dataset
uspto-grants-2014_04
Patent number
US08710223B2

Reaction notes

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