Propargyl bromide → HCID 14851960, compound

HRID 1032785Notes

Reaction equation

HRID 1032785 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1)=[CH:10][C:9]([Cl:17])=[CH:8][CH:7]=3.[O-2].[Ba+2].[CH2:20](Br)[C:21]#[CH:22]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12](=[O:16])[N:13]([CH2:22][C:21]#[CH:20])[C:14]=2[CH:15]=1)=[CH:10][C:9]([Cl:17])=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 2650483,8-Dichloro-6-phenanthridinolHCID 9855530Barium Oxide Nanoparticle Dispersion

Product 1

HCID 14851960HCID 14851960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g (19 mmol) of 3,8-dichloro-6(5H)phenanthridinone, 3,2 g (21 mmol) of barium oxide and 1.9 ml (21 mmol) of propargyl bromide in 40 ml of dimethylformamide was heated on the steam bath for 1 hour. After cooling, the product was precipitated by addition of water, filtered off and washed with water. It was dissolved in methylene chloride and the solution was dried and evaporated. The residue was chromatographed over 150 g of silica gel using 10% (v/v) of hexane in methylene chloride. The fractions containing the product were combined and evaporated. The solid residue was recrystallized from ethanol to give colorless crystals of 3,8-dichloro-5-(2-propynyl)-6(5H)-phenanthridinone with m.p. 248°-250°.

Workup

  1. temperaturewas heated on the steam bath for 1 hour
  2. temperatureAfter cooling
  3. customthe product was precipitated by addition of water
  4. filtrationfiltered off
  5. washwashed with water
  6. dissolutionIt was dissolved in methylene chloride
  7. customthe solution was dried
  8. customevaporated
  9. customThe residue was chromatographed over 150 g of silica gel using 10% (v/v) of hexane in methylene chloride
  10. additionThe fractions containing the product
  11. customevaporated
  12. customThe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-643bb63f153b4337a8435a05c92bcf77
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

Loading…