2-Acetyl-6-methylpyridine → 1-(6-Methylpyridin-2-yl)ethan-1-amine

HRID 1804588

반응식

HRID 1804588 반응식
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[N:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:17].[Na+]>CO>[CH3:10][C:6]1[N:5]=[C:4]([CH:1]([NH2:17])[CH3:2])[CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 1388722-Acetyl-6-methylpyridineHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 232201241-(6-Methylpyridin-2-yl)ethan-1-amine수율 5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-acetyl-6-methylpyridine (4.7 g, 34.8 mmol) in anhydrous methanol (100 ml) was added ammonium acetate (26.8 g, 348 mmol) and sodium cyanoborohydride (1.75 g, 27.8 mmol) and the resulting mixture stirred at RT overnight. The mixture was evaporated and the residue dissolved in water and basified by the addition of KOH and extracted with DCM (×3). The DCM layers were combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on silica to afford the title compound (i-14) (eluent: 5% MeOH in DCM) to give 2.8 g (59%) as a clear oil. 1H NMR (CDCl3): 1.41 (d, J 6.7 Hz, 3H), 1.78 (brs, 2H), 2.54 (s, 3H), 4.21 (q, J 6.7 Hz, 1H), 6.99 (d, J 7.6 Hz, 1H), 7.09 (d, J 7.7 Hz, 1H), 7.52 (m, 1H).

후처리

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in water
  3. additionbasified by the addition of KOH
  4. extractionextracted with DCM (×3)
  5. washwashed with sat. NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica

출처 및 근거

ORD 기록
ord-aa7429a9a02f43bcbf8a180f34a55ddf
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354403B2

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