Hydrazine → 2-Methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=O.[NH2:14][NH2:15].C(OCC)(OCC)(OCC)C>C1(C)C(C)=CC=CC=1>[CH3:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]2[O:7][C:8]([CH3:9])=[N:14][N:15]=2)=[CH:3][C:2]=1[OH:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A suspension of ethyl 3-hydroxy-4-methylbenzoate (3.60 g, 20 mmol) in anhydrous hydrazine (10 mL, 318 mmol) (Aldrich) was heated at reflux (150° C. bath temperature) for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give a dry solid. This was suspended in xylene (50 mL) and concentrated under reduced pressure. The resulting solid was suspended in triethyl ortho-acetate (35 mL, 191 mmol) (Aldrich) and heated at reflux (150° C. bath temperature) for 20 hours with removal of ethanol. After cooling, dichloromethane was added and the solid was collected by filtration to give 2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol as an off-white crystalline material. (Yield 2.28 g).
Workup
- temperaturewas heated
- temperatureAfter cooling to room temperature
- concentrationthe mixture was concentrated under reduced pressure
- customto give a dry solid
- concentrationconcentrated under reduced pressure
- temperatureheated
- temperatureat reflux (150° C. bath temperature) for 20 hours
- customwith removal of ethanol
- temperatureAfter cooling
- additiondichloromethane was added
- filtrationthe solid was collected by filtration
Sources & evidence
- ORD record
- ord-2ed7546fa3f849f19241c453cd7825a8
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968554B2
Reaction notes
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