3-Bromoquinoline → HCID 19697782, compound

HRID 863308Notes

Reaction equation

HRID 863308 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[O:12]1[CH2:16][CH2:15][NH:14][C:13]1=[O:17].C([O-])(=O)C.[K+]>C1(C)C(C)=CC=CC=1.[Cu]>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([N:14]2[CH2:15][CH2:16][O:12][C:13]2=[O:17])[CH:3]=1

Participants

6

Reactant 3

HCID 214133-BromoquinolineHCID 739492-OxazolidinoneHCID 517044Potassium Acetate

Product 1

HCID 19697782HCID 19697782, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7237O-XyleneSolvent

Procedure

26,0 g of 3-bromoquinoline and 4.35 g of 2-oxazolidinone in 200 ml of xylene are heated under reflux in the presence of 7.4 g of potassium acetate and 4.8 g of copper powder for 9 h, analogously to the process of B.Renger in Synthesis (1985) 856. After the mixture has been worked up, the crude product is purified over silica gel with a 500:10:1 mixture of methylene chloride, methanol and concentrated ammonia as the mobile phase, to give 3-(quinolin-3-yl)-2-oxazolidinone as a crystalline solid: Rf (500:10:1 mixture of methylene chloride, methanol and concentrated ammonia)=0.39; FAB-MS: (M+H)+ =215. Hydrogenation of 0.67 g of the resulting product in 10 ml of ethanol in the presence of 0.1 g of palladium-on-charcoal (10% of palladium) at 50° C. in the course of 20 h and FC over 80 g of silica get (mobile phase N) gives 3(R,S)-(2-oxo-oxazolidin-3-yl)-1,2,3,4-tetrahydroquinoline as a white solid: Rf (N)=0.61; MS: M+ =218.

Workup

  1. customthe crude product is purified over silica gel with a 500:10:1 mixture of methylene chloride, methanol and concentrated ammonia as the mobile phase

Sources & evidence

ORD record
ord-77b5c88c792340f885205e794dbe0de9
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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