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

HRID 2369260노트

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HRID 2369260 반응식
[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

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydride2회HCID 462399142-(6-Methyl-pyridin-3-yl)-N-p-tolyl-acetamide

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1afc16e2c0f54ac485b78bbd7dd0f725
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703952B2

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