Ammonium Chloride → 2-Methyl-5-morpholinoaniline

HRID 912326Notes

Reaction equation

HRID 912326 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[N+:14]([O-])=O.[Cl-].[NH4+]>[Zn].CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH2:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 219558884-(4-Methyl-3-nitrophenyl)morpholine

Product 1

HCID 392386232-Methyl-5-morpholinoanilineYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (10 ml) of 4-(4-methyl-3-nitro-phenyl)-morpholine (22 mg) obtained in Step A, zinc (65 mg) and ammonium chloride (16 mg) were added, followed by stirring at room temperature for 3 hours. After filtration through Celite, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (dichloromethane/methanol=30/1), to obtain the desired compound as a colorless solid (17 mg, 90%).

Workup

  1. filtrationAfter filtration through Celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-40e37aa763584756bf801b4c3941d332
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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