Methylhydrazine → HCID 136200892, compound
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction was heated
- temperatureto reflux for 22 hours
- temperatureAfter cooling
- concentrationthe reaction was concentrated in vacuo
- 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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