Urea → 2-Ethyl-5-nitrophenol

HRID 2392647Notes

Reaction equation

HRID 2392647 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1N)[CH3:2].N([O-])=[O:14].[Na+].NC(N)=O.[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[OH:14])[CH3:2]

Participants

7

Reactant 4

HCID 1176UreaHCID 14798Sodium HydroxideHCID 41554782-Ethyl-5-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 189800772-Ethyl-5-nitrophenolYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-ethyl-5-nitroaniline (prepared as described by E. Dyszer et al, Przemysl. Chem 42 (8) 433-5 (1963)) (5 g) in concentrated sulphuric acid (27 ml) and water (160 ml) at 0° C., was treated with sodium nitrite (2.3 g) in water (5 ml) over 5 minutes with stirring. After 1/4 h at 0° C., urea (2 g) was added and the mixture heated to 80° C. for 2 h. After stirring overnight at room temperature, the pH was adjusted to pH 10-12 with 10% sodium hydroxide, and the mixture extracted into ethyl acetate. The organic phase was dried (Na2SO4) and the solvent evaporated under reduced pressure. Flash column chromatography on silica gel, eluting with ethyl acetate and 60°-80° C. petroleum-ether gave the title compound (2.91 g, 58%).

Workup

  1. waitAfter 1/4 h at 0° C.
  2. stirringAfter stirring overnight at room temperature
  3. extractionthe mixture extracted into ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent evaporated under reduced pressure
  6. washFlash column chromatography on silica gel, eluting with ethyl acetate and 60°-80° C. petroleum-ether

Sources & evidence

ORD record
ord-e421eaf942354ad2ae96d9137f0d0465
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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