Ethanolamine → 2-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrile

HRID 419934Notes

Reaction equation

HRID 419934 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:13]([CH2:15][NH2:16])[OH:14]>C(O)C>[OH:14][CH2:13][CH2:15][NH:16][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 217860112-Chloro-3-nitrobenzonitrile

Product 1

HCID 114470952-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-chloro-3-nitrobenzonitrile (74 g, 0.408 mol) is mixed with ethanol (370 ml) and ethanolamine (57 ml). The mixture is stirred for 16 hrs at room temperature. To complete the reaction, the mixture is refluxed for 2 hours. After cooling, the mixture is concentrated under vacuum; the product precipitates as a red solid. To eliminate the ethanolamine hydrochloride salt, the suspension is triturated with 500 ml of water and filtrated under vacuum. The solid is washed with ethanol and ether then dried to give the desired product (75 g, 89%).

Workup

  1. customthe reaction
  2. temperaturethe mixture is refluxed for 2 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated under vacuum
  5. customthe product precipitates as a red solid
  6. customthe suspension is triturated with 500 ml of water
  7. filtrationfiltrated under vacuum
  8. washThe solid is washed with ethanol and ether
  9. customthen dried

Sources & evidence

ORD record
ord-4fe0a309a44c4f9aae3504079b335762
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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