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

HRID 2404859Notes

Reaction equation

HRID 2404859 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12])([CH3:9])([CH3:8])[CH3:7]>OS(O)(=O)=O>[C:6]([C:10]1[CH:16]=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[CH:13][C:11]=1[NH2:12])([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 805742-tert-Butylaniline

Product 1

HCID 8261032-Tert-butyl-5-nitroanilineYield 63%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

KNO3 (7.5 g, 74.18 mmol) in conc. H2SO4 (50 mL) was slowly added to a mixture of 2-tert-butylaniline (11 g, 73.71 mmol) in conc. H2SO4 (50 mL) at −10° C. The mixture was stirred at −10° C. for 1 hour and poured into ice-water. The mixture was extracted with EtOAc (150 mL×3). The combined organics were washed with brine, dried over anhydrous Na2SO4, and purified by silica gel column chromatography to obtain 2-tert-butyl-5-nitro-aniline (9 g, 63%). 1H NMR (400 MHz, CDCl3) δ 7.53 (dd, J=2.8, 8.8 Hz, 1H), 7.46 (d, J=2.8 Hz, 1H), 7.34 (d, J=8.8 Hz, 1H), 4.12 (br s, 2H), 1.44 (s, 9H).

Workup

  1. extractionThe mixture was extracted with EtOAc (150 mL×3)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-40f1269bab8a4388a74b2603aa459529
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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