Morpholine → 5-Morpholino-2-nitroaniline

HRID 1169984Notes

Reaction equation

HRID 1169984 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([CH:14]=1)[NH2:13]>CN(C=O)C>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([NH2:13])[CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 5967255-Morpholino-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

Morpholine (1 equivalent) and 5-chloro-2-nitroaniline (1 equivalent) were dissolved in DMF, and TEA (2 equivalents) was added. The reaction mixture was heated at 120° C. overnight. The reaction mixture was then cooled to room temperature, most of the DMF was distilled off, and water was added to the residue to obtain the crude product as a precipitate. The solid was dried and purified by chromatography on silica gel (2-10% MeOH/CH2Cl2) to afford the desired product, 5-morpholin-4-yl-2-nitro-phenylamine.

Workup

  1. distillationwas distilled off
  2. additionwater was added to the residue
  3. customto obtain the crude product as a precipitate
  4. customThe solid was dried
  5. custompurified by chromatography on silica gel (2-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e83079b7c1134ecaa06993039698bd7d
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

Loading…