HCID 10464590, compound → HCID 22748827, compound

HRID 1780927Notes

Reaction equation

HRID 1780927 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].ClC1C(O)=C[C:10]2=[CH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N+:17]=3[CH:18]=[C:9]2C=1.O1C=CC(C(C2C=COC=2)=C)=C1>C(#N)C>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH:13]1[C:12]2[N+:17](=[CH:18][CH:9]=[CH:10][CH:11]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 10464590HCID 10464590, compoundHCID 19047487HCID 19047487, compound

Product 1

HCID 22748827HCID 22748827, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture containing 8-chloro-9-hydroxybenzo[b]quinolizinium perchlorate (3.3 g; 10 mmol) and 1,1-di(3-furyl)ethylene (1.76 g, 11 mmol) in 50 ml of acetonitrile was allowed to reflux under nitrogen with stirring for 6 hours. The reaction mixture was concentrated in vacuo and the residue was crystallized from methylene chloride/ethyl acetate/methanol (7:2:1). The solid product was purified by silica gel chromatography (9:1 methylene chloride/methanol) to afford 3.3 g of 6,11-ethano-12,12-di(3-furyl)-9-chloro-10-hydroxy-6,11-dihydrobenzorb]quinolizinium perchlorate (Formula I: R1 =R2 =R3 =R4 =H; R5 =R6 =3-furyl; R7 =9-Cl; 10-OH; X- =ClO4-) as a solid.

Workup

  1. temperatureto reflux under nitrogen
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was crystallized from methylene chloride/ethyl acetate/methanol (7:2:1)
  4. customThe solid product was purified by silica gel chromatography (9:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-d5f647c0f6554e4d83d12e046e00e776
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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