Cesium carbonate → HCID 21104297, compound

HRID 1675185Notes

Reaction equation

HRID 1675185 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cl:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:14]=1Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:14]=1[O:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 113763-HydroxyquinolineHCID 883653,4,5-Trichloronitrobenzene

Product 1

HCID 21104297HCID 21104297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxyquinoline (1) (prepared according to the procedure of Naumann et. al., Synthesis 4:279-281 (1990)) (3 g) and 1,2,3-trichloro-5-nitrobenzene (4.7 g) were dissolved in DMF (80 mL) and heated with cesium carbonate (7.4 g) for 2 h at 60° C. The reaction was poured into ice/water (500 mL). The resulting off-white precipitate was collected by filtration and rinsed with hexane to afford compound II as a solid (6.9 g) suitable for use in the next reaction.

Workup

  1. filtrationThe resulting off-white precipitate was collected by filtration
  2. washrinsed with hexane

Sources & evidence

ORD record
ord-acd655af800e46db9d7109f67ad2402f
Source dataset
uspto-grants-2011_08
Patent number
US08003665B2

Reaction notes

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