Morpholine → 5-Morpholino-2-nitroaniline

HRID 1465799Notes

Reaction equation

HRID 1465799 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[O:15]1[CH2:16][CH2:17][N:12]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 5967255-Morpholino-2-nitroanilineYield 584.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (4.0 g, 2.3 mmol), morpholine (3.45 ml, 41 mmol) and anhydrous potassium carbonate (3.2 g, 23 mmol) in N,N-dimethylacetamide (40 ml) was stirred at 130-140° C. under nitrogen overnight. The reaction mixture was then cooled to room temperature, poured onto ice and allowed to stand for 2-3 h. The yellow-brown precipitate was collected by filtration to afford 5-morpholino-2-nitroaniline (3.0 g, 58%), mp 183-185° C. (lit. (8) mp 187.5° C.).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. additionpoured onto ice
  3. waitto stand for 2-3 h
  4. filtrationThe yellow-brown precipitate was collected by filtration

Sources & evidence

ORD record
ord-b8ae80e6b0884db39a65f92c5c633fba
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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