Potassium Nitrate → 2-Tert-butyl-5-nitroaniline

HRID 2189583Notes

Reaction equation

HRID 2189583 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 805742-tert-Butylaniline

Product 1

HCID 8261032-Tert-butyl-5-nitroanilineYield 64%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

To a cooled solution of sulfuric acid (90%, 50 mL) was added dropwise 2-tert-butyl-phenylamine (4.5 g, 30 mmol) at 0° C. Potassium nitrate (4.5 g, 45 mmol) was added in portions at 0° C. The reaction mixture was stirred at 0-5° C. for 5 min, poured into ice-water and then extracted with EtOAc three times. The combined organic layers were washed with brine and dried over Na2SO4. After removal of solvent, the residue was purified by recrystallization using 70% EtOH—H2O to give 2-tert-butyl-5-nitroaniline (3.7 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=8.7, 2.4 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 4.17 (s, 2H), 1.46 (s, 9H); HPLC ret. time 3.27 min, 10-99% CH3CN, 5 min run; ESI-MS 195.3 m/z (MH+).

Workup

  1. extractionextracted with EtOAc three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent
  5. customthe residue was purified by recrystallization

Sources & evidence

ORD record
ord-94752b4aa1734bcda4b8d6d50f63ad84
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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