Cesium carbonate → HCID 58167832, compound

HRID 1915043Notes

Reaction equation

HRID 1915043 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=1>CS(C)=O.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([Cl:15])[CH:21]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 115683-AminophenolHCID 335152,4-Dichloropyridine

Product 1

HCID 58167832HCID 58167832, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-aminophenol (3.7 g, 34.09 mmol) in DMSO (50 mL) was added Cs2CO3 (30.7 g, 94.46 mmol). The mixture stirred for 10 minutes and then 2,4-dichloropyridine (5.0 g, 33.79 mmol) was added. The mixture was stirred at 120° C. for 1.5 h. The mixture was cooled and diluted with water. The aqueous solution was extracted with EtOAc (3×100 mL). The organic extracts were combined, dried over MgSO4 and concentrated to afford a dark oil. The oil was purified via column chromatography, eluting with 30-40% EtOAc/hexanes, to afford 4-(3-Aminophenoxy)-2-chloropyridine (6.63 g, 89%) as a brown solid.

Workup

  1. stirringThe mixture was stirred at 120° C. for 1.5 h
  2. temperatureThe mixture was cooled
  3. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto afford a dark oil
  7. customThe oil was purified via column chromatography
  8. washeluting with 30-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-54aa74fdd73e446f88ba4a4071881180
Source dataset
uspto-grants-2013_12
Patent number
US08614234B2

Reaction notes

Loading…