Acetaldehyde → N-Ethyl-6-methylpyridin-2-amine

HRID 1771310Notes

Reaction equation

HRID 1771310 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[CH:9](=O)[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(O)(=O)C>[CH2:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1)[CH3:10]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 157652-Amino-6-methylpyridineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 3016051N-Ethyl-6-methylpyridin-2-amineYield 51%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

2-Amino-6-methylpyridine (1.00 g, 9.25 mmol) and acetaldehyde (0.52 mL, 9.34 mmol) were stirred together in anhydrous methyl alcohol for 1 hour at room temperature under a nitrogen atmosphere. The mixture was then treated with sodium triacetoxyborohydride (7.84 g, 37.0 mmol) and five drops of acetic acid and all was allowed to continue stirring for 4 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between water and DCM, and the separated aqueous phase was extracted twice with DCM. The combined organics were dried over MgSO4, filtered and concentrated in vacuo to give a mobile oil which was purified by flash column chromatography, eluting with 2% MeOH/DCM, to give 2-ethylamino-6-methylpyridine (636 mg, 51%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between water and DCM
  3. extractionthe separated aqueous phase was extracted twice with DCM
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a mobile oil which
  8. customwas purified by flash column chromatography
  9. washeluting with 2% MeOH/DCM

Sources & evidence

ORD record
ord-3913c5c40e4f4c62b4e450f0f4a3c8b7
Source dataset
uspto-grants-2016_02
Patent number
US09249130B2

Reaction notes

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