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

HRID 2089119Notes

Reaction equation

HRID 2089119 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([NH2:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO.[Pd]>[O:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:12]=[C:11]([NH2:13])[C:10]([NH2:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 5967255-Morpholino-2-nitroaniline

Product 1

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamineYield 108.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.1 g of 10% Pd/C was added to 1.0 g of 5-morpholin-4-yl-2-nitro-phenylamine (4.3 mmol) dissolved in 43 mL of methanol, and allowed to stir under hydrogen balloon at room temperature for 4 hours. The mixture was filtered with diatomaceous earth to remove the catalyst, and concentrated under reduced pressure to obtain 0.9 g of 4-morpholinobenzene-1,2-diamine (yield 100%).

Workup

  1. filtrationThe mixture was filtered with diatomaceous earth
  2. customto remove the catalyst
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ec2c88f185345a9b478269512d0e95b
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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