Sodium Hydroxide → HCID 21827055, compound

HRID 1669169Notes

Reaction equation

HRID 1669169 reaction equation
[N+:1]([C:4]1[C:13]([NH:14]C(=O)C)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][O:9]2)([O-:3])=[O:2].[OH-].[Na+]>CCO>[N+:1]([C:4]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][O:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21827041HCID 21827041, compound

Product 1

HCID 21827055HCID 21827055, compoundYield 151.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of acetamide 231 (1.24 g, 5.25 mmol) in 95% EtOH (50 mL) and NaOH (0.63 g, 15.7 mmol) was stirred at reflux temperature for 16 h. The mixture was cooled and the solvent evaporated. The residue was partitioned between Et2O and water, the organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with 20% EtOAc/pet. ether, to give nitroaniline 233 (1.54 g, 85%) as red oil: 1H NMR δ 6.85 (d, J=9.0 Hz, 1H, H-8), 6.60 (d, J=9.0 Hz, 1H, H-7), 4.90 (br s, 2H, NH2), 4.13 (dd, J=5.3, 5.1 Hz, 2H, H-2), 2.90 (br t, J=6.5 Hz, 2H, H-4), 1.91-1.96 (m, 2H, H-3).

Workup

  1. temperatureat reflux temperature for 16 h
  2. temperatureThe mixture was cooled
  3. customthe solvent evaporated
  4. customThe residue was partitioned between Et2O and water
  5. customthe organic fraction dried
  6. customthe solvent evaporated
  7. customThe residue was purified by chromatography
  8. washeluting with 20% EtOAc/pet. ether

Sources & evidence

ORD record
ord-1e93f33432374f8b87fa88be749e811f
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

Loading…