Bromine → methyl 2-bromo-4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

HRID 648529Notes

Reaction equation

HRID 648529 reaction equation
[O:1]=[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([C:18]([O:20][CH3:21])=[O:19])=[C:8]2[N:3]1[CH2:4][CH2:5][C:6]1[CH:24]=[CH:23][S:22][C:7]=12.[Br:25]Br>C(Cl)(Cl)Cl>[Br:25][C:23]1[S:22][C:7]2[C:8]3[N:3]([CH2:4][CH2:5][C:6]=2[CH:24]=1)[C:2](=[O:1])[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:10][C:9]=3[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 24408BromineHCID 14666687methyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

Product 1

HCID 19020479methyl 2-bromo-4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1.8 g of methyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate are dissolved in 32 ml of chloroform, whereupon the solution was treated at 0° with 0.55 ml of bromine in 1 ml of chloroform and stirred at room temperature overnight. After washing with 2N sodium hydroxide solution and saturated sodium chloride solution, drying over magnesium sulfate and evaporation, the residue in toluene/ethyl acetate (4:1) was chromatographed on silica gel. There was obtained pure methyl 2-bromo-4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate of m.p. 170.5°-171° (from isopropanol).

Workup

  1. washAfter washing with 2N sodium hydroxide solution and saturated sodium chloride solution
  2. dry with materialdrying over magnesium sulfate and evaporation
  3. customthe residue in toluene/ethyl acetate (4:1) was chromatographed on silica gel

Sources & evidence

ORD record
ord-1980bd5bfa2c4764a96cee922ae89e63
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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