Urea → Benzenamine, 4-methoxy-3-nitro-

HRID 51859

Reaction equation

HRID 51859 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.NC(N)=O.[N+:14]([O-])([O-:16])=[O:15].[K+].[OH-].[Na+]>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 1176UreaHCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 24434Potassium Nitrate

Product 1

HCID 123071Benzenamine, 4-methoxy-3-nitro-Yield 77%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
7.5 °C

Procedure

To a stirred solution of 30.0 g (244 mmol) p-anisidine in 105 ml concentrated sulfuric acid at 0° C. was added 17.6 g (292 mmol) urea. After stirring for 1 h, a solution of 27.1 g (268 mmol) potassium nitrate in 47 ml concentrated sulfuric acid was then added dropwise over 1 h while the reaction mixture was maintained at 5-10° C. The mixture was then poured onto ice, and sodium hydroxide pellets added portionwise with stirring until the pH was 14. Ethyl acetate was then added and the phases were separated. The organic phase was washed with water and then with brine, dried over sodium sulfate, and concentrated in vacuo to afford 31.4 g (77%) 4-methoxy-3-nitro-phenylamine as an orange solid. EI-MS m/e (%): 169 (M+, 100), 153 ([M-CH3]+, 10), 92 (21).

Workup

  1. additionadded portionwise
  2. stirringwith stirring until the pH was 14
  3. customthe phases were separated
  4. washThe organic phase was washed with water
  5. dry with materialwith brine, dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3efeb78626247de87e868c249c3882b
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

Loading…