Methylhydrazine → HCID 136200892, compound

HRID 1619690Notes

Reaction equation

HRID 1619690 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[CH:6][C:5]2=O.[CH3:13][NH:14][NH2:15].B(F)(F)F.CCOCC>C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:8])=[C:4]([C:5]2[N:14]([CH3:13])[N:15]=[CH:7][CH:6]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 8000Boron trifluoride etherateHCID 5485226-Bromochromone

Product 1

HCID 136200892HCID 136200892, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6-bromochromone (1.58 g, 0.0070 mol) in ethanol (30 mL) was added methylhydrazine (0.41 mL, 0.0077 mol) and boron trifluoride etherate (1.15 mL, 0.0091 mol). The reaction was heated to reflux for 22 hours. After cooling, the reaction was concentrated in vacuo and the residue purified by automated flash column chromatography using a 0-100% ethyl acetate/hexanes gradient. This provided the title compound (0.79 g, 44%) as a light yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 22 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction was concentrated in vacuo
  5. customthe residue purified by automated flash column chromatography

Sources & evidence

ORD record
ord-1894b90a44964114a499aa094415f0bf
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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