Potassium Nitrate → N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamide

HRID 1014403Notes

Reaction equation

HRID 1014403 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:13])[CH3:12].[N+:14]([O-])([O-:16])=[O:15].[K+]>C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[NH:10][C:11](=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 24434Potassium NitrateHCID 95082N-(4-Methoxy-2-methylphenyl)-acetamide

Product 1

HCID 21260362N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamideYield 46.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-[2-methyl-4-(methyloxy)phenyl]acetamide (1.95 g, 10.88 mmol) was dissolved in TFA (20 mL) and cooled to 0° C. in an ice bath. Potassium nitrate (1.210 g, 11.97 mmol) was added slowly. The reaction was monitored by tic and quenched by pouring into ice and diluting with EtOAc. A solution of saturated sodium bicarbonate was added until solution was a neutral pH. Organics were washed with water and saturated brine solution and dried over sodium sulfate. Solvents were removed under reduced pressure to afford a yellow solid. Efforts to dissolve the solid in ethyl acetate resulted in a suspension that was let sit for several hours. Hexanes were added and the solids filtered to afford N-[2-methyl-4-(methyloxy)-5-nitrophenyl]acetamide (1.13 g, 5.04 mmol) as yellow fluffy solid. The filtrate was purified via SiO2 chromatography to afford N-[2-methyl-4-(methyloxy)-5-nitrophenyl]acetamide (1.02 g, 4.55 mmol) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.00-2.11 (m, 3 H) 2.29 (s, 3 H) 3.90 (s, 3 H) 7.24 (s, H) 7.99 (s, 1 H) 9.42 (s, 1 H)

Workup

  1. customquenched
  2. additionby pouring into ice
  3. additiondiluting with EtOAc
  4. additionA solution of saturated sodium bicarbonate was added until solution
  5. washOrganics were washed with water and saturated brine solution
  6. dry with materialdried over sodium sulfate
  7. customSolvents were removed under reduced pressure
  8. customto afford a yellow solid
  9. customresulted in a suspension that
  10. waitwas let sit for several hours
  11. filtrationthe solids filtered

Sources & evidence

ORD record
ord-b239e9e3d37948bbb39beaa5c9cb3b6f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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