Acetic Acid → N,N,4-Trimethylpyridin-2-amine

HRID 1360377Notes

Reaction equation

HRID 1360377 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[BH3-][C:10]#[N:11].[Na+].C=O.[C:15](O)(=O)C>C(#N)C.O>[CH3:15][N:11]([CH3:10])[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 15332-Amino-4-methylpyridineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18797061N,N,4-Trimethylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-amino-4-picoline (33 g), NaBH3CN (57 g), formaldehyde (37% aq. solution, 240 mL) in acetonitrile (1 L) and water (200 mL) was added dropwise acetic acid (60 mL) at 0° C. in 2 hr. The resultant solution was stirred at RT for 7 days and then concentrated in vacuo. The residue was basified with solid NaOH to pH 10 and extracted with hexanes (3×700 mL). The combined extract was washed with 1N aq. NaOH and brine, dried over Na2SO4 and evaporated in vacuo to give 2-dimethylamino-4-methylpyridine as a colorless oil (Cmpd 1a, 36 g, 88%). 1H NMR (CDCl3): 2.26 (s, 3H), 3.07 (s, 6H), 6.33 (s, 1H), 6.40 (d, 1H), 8.02 (d, 1H); MS (CI) m/e 137 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with hexanes (3×700 mL)
  3. extractionThe combined extract
  4. washwas washed with 1N aq. NaOH and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f40189d458154366aeea28bb7ac5668b
Source dataset
uspto-grants-2011_02
Patent number
US07879862B2

Reaction notes

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