1-(2,3-Dihydroxypropylaminocarbonyl)-3-nitro-5-(1,2-dihydroxyethyl)benzene → 3-(2,3-Dihydroxypropylaminocarbonyl)-5-(1,2-dihydroxyethyl)aniline

HRID 1280139Notes

Reaction equation

HRID 1280139 reaction equation
[OH:1][CH:2]([CH2:20][OH:21])[CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([CH:13]([OH:16])[CH2:14][OH:15])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=1)=[O:6]>CO.O.[Pd]>[OH:1][CH:2]([CH2:20][OH:21])[CH2:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([CH:13]([OH:16])[CH2:14][OH:15])[CH:12]=1)[NH2:17])=[O:6]

Participants

5

Reactant 1

HCID 184293651-(2,3-Dihydroxypropylaminocarbonyl)-3-nitro-5-(1,2-dihydroxyethyl)benzene

Product 1

HCID 184292253-(2,3-Dihydroxypropylaminocarbonyl)-5-(1,2-dihydroxyethyl)aniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(2,3-Dihydroxypropylaminocarbonyl)-3-nitro-5-(1,2-dihydroxyethyl)benzene (0.40 g, 1.32 mmol) was dissolved in a mixture of methanol (40 ml) and water (20 ml). The solution was hydrogenated at 60 psi using a Pd/C catalyst (10%, 50 mg). The solution was filtered through celite and the solvents were removed by evaporation. The product was >95% pure by HPLC analysis and was used without further purification.

Workup

  1. filtrationThe solution was filtered through celite
  2. customthe solvents were removed by evaporation
  3. customwas used without further purification

Sources & evidence

ORD record
ord-90036f8361d14fe696173ecdd1e25c30
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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