3-(4-Hydroxyphenyl)propionic acid → HCID 58674472, compound

HRID 1994135Notes

Reaction equation

HRID 1994135 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.C(=O)([O-])[O-:11].[Cs+].[Cs+].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:19][CH:18]=1>CN(C=O)C>[NH2:9][C:8]([C:4]1[CH:3]=[C:2]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH:7]=[CH:6][N:5]=1)=[O:11]

Participants

5

Reactant 3

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 10796Cesium carbonateHCID 6933424-Chloro-2-pyridinecarbonitrile

Product 1

HCID 58674472HCID 58674472, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloropyridine-2-carbonitrile (2.0 g, 14.5 mmol) in DMF (70 mL) was added cesium carbonate (14.0 g, 43.5 mmol) and 3-(4-hydroxyphenyl)propanoic acid (2.6 g, 15.9 mmol). The reaction mixture was heated at reflux overnight. The mixture was cooled to rt, concentrated, and then taken up in 300 mL of water. The pH was adjusted to 3 by the dropwise addition of oxalic acid and a precipitate formed. The precipitate was filtered to yield the title compound as a brown solid (1.2 g, 28%). LCMS: Method FA, Rt=1.27 min, [MH+=287].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated
  4. additionThe pH was adjusted to 3 by the dropwise addition of oxalic acid
  5. customa precipitate formed
  6. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-26befea14383405d89ec344b2d25f3df
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

Loading…