Ethanolamine → 2-Chloro-4-phenyl-6-(2-hydroxyethylamino)-3,5-pyridinedicarbonitrile

HRID 2264524Notes

Reaction equation

HRID 2264524 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([Cl:18])[N:3]=1.N[CH2:20][CH2:21][OH:22]>C1COCC1>[Cl:18][C:4]1[C:5]([C:16]#[N:17])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C:8]#[N:9])=[C:2]([NH:1][CH2:20][CH2:21][OH:22])[N:3]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 27867132-amino-6-chloro-4-phenylpyridine-3,5-dicarbonitrile

Product 1

HCID 179760112-Chloro-4-phenyl-6-(2-hydroxyethylamino)-3,5-pyridinedicarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (3.65 mmol) of 2,6-dichloro-4-phenyl-3,5-pyridinedicarbonitrile [Quintela et al., Heterocycles 38, 1299-1305 (1994)] is, together with 0.33 g (5.47 mmol) of 2-aminoethanol, dissolved in 3 ml of THF, and the mixture is heated under reflux for 8 h. The reaction mixture is purified by preparative HPLC on reversed-phase silica gel (gradient: water+0.1% formic acid/acetonitrile 90:105:95 in 35 minutes).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 8 h
  3. customThe reaction mixture is purified by preparative HPLC on reversed-phase silica gel (gradient: water+0.1% formic acid/acetonitrile 90:105:95 in 35 minutes)

Sources & evidence

ORD record
ord-3b4efe94768649129aad4878d4bd86a6
Source dataset
uspto-grants-2010_12
Patent number
US07855219B2

Reaction notes

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