Potassium Nitrate → 4-(Tert-butyl)-3-nitroaniline

HRID 74027Notes

Reaction equation

HRID 74027 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-])([O-:14])=[O:13].[K+].C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][C:10]=1[N+:12]([O-:14])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24434Potassium NitrateHCID 698614-Tert-ButylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 3161634-(Tert-butyl)-3-nitroanilineYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 4-tert-butyl-phenylamine (10.0 g, 67.01 mmol) dissolved in H2SO4 (98%, 60 mL) was slowly added KNO3 (8.1 g, 80.41 mmol) at 0° C. After addition, the reaction was allowed to warm to room temperature and stirred overnight. The mixture was then poured into ice-water and basified with sat. NaHCO3 solution to pH 8. The mixture was extracted several times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc, 10:1) to give 4-tert-butyl-3-nitro-phenylamine (10 g, 77%).

Workup

  1. customat 0° C
  2. additionAfter addition
  3. extractionThe mixture was extracted several times with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 10:1)

Sources & evidence

ORD record
ord-99ae287ebab64734b6fc2617f45af051
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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