2-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrile → 3-Amino-2-[(2-hydroxyethyl)amino]benzonitrile

HRID 419935Notes

Reaction equation

HRID 419935 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[H][H]>[Pd].CO>[NH2:13][C:12]1[C:5]([NH:4][CH2:3][CH2:2][OH:1])=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 114470952-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 582984983-Amino-2-[(2-hydroxyethyl)amino]benzonitrileYield 106.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methanol (500 ml) and Pd/activated charcoal 5% (wet, 3.45 g) are added to 2-[(2-hydroxyethyl)amino]-3-nitrobenzonitrile (69 g, 0.333 mol). The suspension is shaken in a Parr apparatus under 20 psi pressure of hydrogen for 1 hour. The mixture is then filtered on Celite and evaporated to dryness to give the desired material (62.7 g). This product is used in the next step without further purification.

Workup

  1. filtrationThe mixture is then filtered on Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-1e16d104712e47599c2f1eab463aeca0
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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