Potassium Nitrate → 4-[2-(2-Methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenylamine

HRID 74014Notes

Reaction equation

HRID 74014 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:9])[CH3:8].[N+:17]([O-])([O-:19])=[O:18].[K+]>OS(O)(=O)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 574826984-[2-(2-Methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenylamine

Product 1

HCID 575673834-[2-(2-Methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenylamineYield 71.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenylamine (5.8 g, 26 mmol) in H2SO4 (20 mL) was added KNO3 (2.63 g, 26 mmol) at 0° C. After addition was complete, the mixture was stirred at this temperature for 20 min and then poured into ice-water. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc, 100:1) to give 4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenylamine (5 g, 71%).

Workup

  1. additionAfter addition
  2. extractionThe mixture was extracted with EtOAc (50 mL×3)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 100:1)

Sources & evidence

ORD record
ord-6b198b8d8ad0483c89910b4f70bce9f2
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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