Methylhydrazine → HCID 136049327, compound

HRID 1296953Notes

Reaction equation

HRID 1296953 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=O)[C:16]3[C:11](=[CH:12][C:13]([OH:20])=[C:14]([Cl:19])[CH:15]=3)[O:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:21][NH:22][NH2:23]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:16]3[CH:15]=[C:14]([Cl:19])[C:13]([OH:20])=[CH:12][C:11]=3[OH:10])=[N:23][N:22]([CH3:21])[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 58913628HCID 58913628, compound

Product 1

HCID 136049327HCID 136049327, compoundYield 73%

Procedure

An ethanolic solution (5 ml) of 3-(4-Bromo-phenyl)-6-chloro-7-hydroxy-chromen-4-one (100 mg, 28 mmol) was heated to boiling, methyl hydrazine (0.30 ml, 20 equiv.) added in one portion, and refluxing continued for 16 hrs. After cooling, the volatiles were evaporated under reduced pressure and water added to the residue causing a precipitate to form. This was filtered off and dried under vacuum in the presence of P2O5 to provide 78 mg (73% yield) as a tan coloured powder. Although pure by LCMS further purification by column chromatography, eluting with first 40% EtOAc in Hexane and increasing to 60%, gave a grey-white powder (6 mg). The exact regioisomer was confirmed by NOESY 1H NMR.

Workup

  1. temperaturerefluxing
  2. temperatureAfter cooling
  3. customthe volatiles were evaporated under reduced pressure and water
  4. additionadded to the residue
  5. customto form
  6. filtrationThis was filtered off
  7. dry with materialdried under vacuum in the presence of P2O5
  8. customto provide 78 mg (73% yield) as a tan coloured powder
  9. customAlthough pure by LCMS further purification by column chromatography
  10. washeluting with first 40% EtOAc in Hexane
  11. temperatureincreasing to 60%

Sources & evidence

ORD record
ord-a85352ba80db4be6964f75ec523eec49
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

Loading…