Ethanol → 5-ethoxy-2-nitroaniline

HRID 272717Notes

Reaction equation

HRID 272717 reaction equation
[Na].Cl[C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([CH:9]=1)[NH2:8].[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([CH:9]=1)[NH2:8])[CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 742185-Chloro-2-nitroanilineHCID 5360545Sodium2×

Product 1

HCID 51417895-ethoxy-2-nitroanilineYield 94%

Conditions

Temperature
80 °C

Procedure

A mixture of sodium metal (1.86 g, 80.9 mmol) and ethanol (65 mL) was stirred at ambient temperature until all of the sodium metal had been consumed. 5-Chloro-2-nitroaniline (4.64 g, 26.9 mmol) was added and the mixture was heated at 80° C. for 48 hours, cooled to room temperature, quenched with water, concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel with 7:3 hexane/ethyl acetate to provide 4.6 g (94%) of the desired product. MS (ESI) m/e 183 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 7.90 (d, J=9.5 Hz, 1H), 7.46 (br s, 2H), 6.43 (d, J=2.7 Hz, 1H), 6.23 (dd, J=2.7, 9.5 Hz, 1H), 4.04 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H).

Workup

  1. customhad been consumed
  2. temperaturecooled to room temperature
  3. customquenched with water
  4. concentrationconcentrated under vacuum
  5. additiondiluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by column chromatography on silica gel with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-69d3a98b3e5440f0b5e0634bc21a6715
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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