Diethyl Ether → 4-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline

HRID 2369260Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=O)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>C1COCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:11][C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(6-Methyl-pyridin-3-yl)-N-p-tolyl-acetamide (0.960 g, 4 mmol) was dissolved in dry THF (20 cm3), and cooled to 0° C. LiAlH4 (5.0 eq., 20 mmol, 10 ml of a 2.0 M solution in THF) was added dropwise at first, until no more gas evolution was observed (˜0.5 ml), and then the remaining LiAlH4 solution was added in one portion. The resulting solution was heated to reflux for 16 hours with stirring. Wet diethyl ether was then added until no further gas evolution was observed, the resulting medium filtered, and the residue washed with ether (˜50 cm3). The filtrate was dried (MgSO4), and the solvent removed to yield a crude yellow oil. The oil was purified by flash chromatography, eluting with 1:1 petrol (40-60)/EtOAc. The product was collected as the fraction with Rf=0.294. The product was obtained as a pale yellow oil (254 mg, 28%).

Workup

temperatureThe resulting solution was heated
temperatureto reflux for 16 hours
filtrationthe resulting medium filtered
washthe residue washed with ether (˜50 cm3)
dry with materialThe filtrate was dried (MgSO4)
customthe solvent removed
customto yield a crude yellow oil
customThe oil was purified by flash chromatography
washeluting with 1:1 petrol (40-60)/EtOAc
customThe product was collected as the fraction with Rf=0.294

Sources & evidence

ORD record: ord-1afc16e2c0f54ac485b78bbd7dd0f725
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703952B2

Reaction notes

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