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5-Chloro-8-hydroxyquinoline → 8-(2-Hydroxyethyl)5-chloroquinoline

HRID 1025536
Notes
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Reaction equation

HRID 1025536 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9](O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C1(=O)O[CH2:16][CH2:15][O:14]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:14][CH2:15][CH2:16][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 28175-Chloro-8-hydroxyquinolineHCID 7303Ethylene carbonateHCID 10796Cesium carbonate

Product 1

HCID 452801778-(2-Hydroxyethyl)5-chloroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-8-hydroxyquinoline (1 mmol, 180 mg), ethylene carbonate (2 mmol, 180 mg) and Cs2CO3 (0.6 mmol, 195 mg) in dry DMF (10 mL) was stirred vigorously at 120° C. for 3 h. DMF was evaporated under high-vacuum and the residue was dissolved in water (15 mL), extracted twice with dichloromethane (15 mL), and the residue left after evaporation of dichloromethane was chromatographed over silica gel (eluent: 4:1 hexanes-EtOAc). A biege colored solid was obtained (174 mg, 78%).

Workup

  1. customDMF was evaporated under high-vacuum
  2. dissolutionthe residue was dissolved in water (15 mL)
  3. extractionextracted twice with dichloromethane (15 mL)
  4. waitthe residue left
  5. customafter evaporation of dichloromethane
  6. customwas chromatographed over silica gel (eluent: 4:1 hexanes-EtOAc)
  7. customwas obtained (174 mg, 78%)

Sources & evidence

ORD record
ord-fa988a59dc914388a1cf80dbb5cb3d0e
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729097B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes