5-Morpholino-2-nitroaniline → 4-(Morpholin-4-yl)benzene-1,2-diamine

HRID 1465800Notes

Reaction equation

HRID 1465800 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])[CH2:3][CH2:2]1>[Pd].C(OCC)(=O)C.CO>[NH2:12][C:11]1[CH:13]=[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH:8]=[CH:9][C:10]=1[NH2:14]

Participants

4

Reactant 1

HCID 5967255-Morpholino-2-nitroaniline

Product 1

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 5-morpholino-2-nitroaniline (0.50 g, 2.2 mmol) in 4:1 ethyl acetate/methanol (25 ml) was added 5% palladium on carbon (0.11 g) and the reaction mixture stirred under an atmosphere of hydrogen overnight. The reaction mixture was then filtered through celite, the filtered solid washed with methanol, and the combined filtrate and washings concentrated in vacuo to give the crude 2-amino-4-morpholinoaniline which was used immediately for the next step.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washthe filtered solid washed with methanol
  3. concentrationthe combined filtrate and washings concentrated in vacuo

Sources & evidence

ORD record
ord-d394925401434e25ad1a6c797b5aff37
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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