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

HRID 1804588Notes

Reaction equation

HRID 1804588 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aa7429a9a02f43bcbf8a180f34a55ddf
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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