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

HRID 2369260ノート

反応式

HRID 2369260 の反応式
[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

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydride2 回HCID 462399142-(6-Methyl-pyridin-3-yl)-N-p-tolyl-acetamide

生成物 1

HCID 7784464-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline収率 28.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-1afc16e2c0f54ac485b78bbd7dd0f725
出典データセット
uspto-grants-2014_04
特許番号
US08703952B2

反応ノート

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