3-Nitroaniline → 4-(3-Nitrophenyl)morpholine

HRID 742335

Reaction equation

HRID 742335 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:7]1([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8115Bis(2-chloroethyl) ether3×HCID 11430Potassium Carbonate

Product 1

HCID 12532734-(3-Nitrophenyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Nitroaniline (10 g, 72 mmol)in DMF (100 ml) was added bis(2-chloroethyl) ether (11.7 ml, 100 mmol) and potassium carbonate (27.6 g, 200 mmol). The mixture was heated to reflux for 10 hours. Additional bis(2-chloroethyl) ether (3 ml) was added and reflux was maintained for 18 hours. Addition of bis(2-chloroethyl) ether was repeated and reflux was continued for 4 hours. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic phase was dried and evaporated. The residue was extracted with diethyl ether. The extract was concentrated and purified by column chromatography on silica gel with ethyl acetate/petroleum ether (3:7) as the eluent. Yield 3.4 g. Mp 87°-90° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 hours
  3. temperaturereflux
  4. temperaturewas maintained for 18 hours
  5. temperaturereflux
  6. customThe solvent was evaporated
  7. customthe residue partitioned between water and ethyl acetate
  8. customThe organic phase was dried
  9. customevaporated
  10. extractionThe residue was extracted with diethyl ether
  11. concentrationThe extract was concentrated
  12. custompurified by column chromatography on silica gel with ethyl acetate/petroleum ether (3:7) as the eluent

Sources & evidence

ORD record
ord-3736e5ea3c2042bc8281679e5d79cd9c
Source dataset
uspto-grants-1996_09
Patent number
US05554630

Linked notes

Loading…