4-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]-N-nitrosoaniline → 1-(4-Methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=O)=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[NH2:11])=[CH:6][CH:7]=1Participants
Procedure
Crude 2-methyl-5-(N-nitroso-2-p-tolylaminoethyl)pyridine (612 mg, 2.4 mmol) was dissolved in dry THF (20 cm3) in a dry 3-neck flask under an argon atmosphere and cooled until the internal temperature was between 0-5° C. Solid LiAlH4 (290 mg, 7.7 mmol) was added and the reaction allowed to warm to room temperature. Following 2 hours stirring at room temperature, the reaction was again cooled to 0° C., and quenched with MeOH until no further gas evolution was observed (˜3 cm3). Saturated NaOH solution was then added (3 cm3), followed by H2O (3 cm3), and the medium extracted with CHCl3 (3×50 cm3), the combined extracts were dried (MgSO4), and solvent removed in vacuo to yield a crude orange oil. This could be carried forward to the next step if desired, or stored below 5° C. until required.
Workup
- temperaturecooled until the internal temperature
- customwas between 0-5° C
- temperaturethe reaction was again cooled to 0° C.
- customquenched with MeOH until no further gas evolution
- additionSaturated NaOH solution was then added (3 cm3)
- extractionthe medium extracted with CHCl3 (3×50 cm3)
- dry with materialthe combined extracts were dried (MgSO4), and solvent
- customremoved in vacuo
- customto yield a crude orange oil
- customstored below 5° C.
Sources & evidence
- ORD record
- ord-23b94f2f9b5847ec82b7a2067c9bdc55
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703952B2
Reaction notes
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