Acetic Anhydride → 3-(Acetamidomethyl)pyridine

HRID 708339Notes

Reaction equation

HRID 708339 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[O:11])[CH3:10])[CH:2]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 310183-Pyridinemethanamine

Product 1

HCID 27352253-(Acetamidomethyl)pyridineYield 102.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared according to Plater et al. Org. Biomol. Chem. 2009, 7, 1633. To a solution of pyridin-3-ylmethanamine (9.42 ml, 92 mmol) in water (103 ml) at 10° C. was added acetic anhydride (10.47 ml, 111 mmol), stirred at a rate where the internal temperature did not rise above 25° C. After an additional 18 h of stirring, the solution was concentrated in vacuo then co-evaporated with toluene (3×) to afford the title compound (14.22 g, quantitative) as a clear oil. LCMS: Rt=0.12 min, m/z=151.1 (M+1) Method 2m_acidic. 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=2.4 Hz, 2H) 7.65 (dd, J=7.8, 1.6 Hz, 1H) 7.30-7.24-(m, 1H) 6.59-6.49 (m, 1H) 4.43 (d, J=6.0 Hz, 2H) 2.02 (s, 3H).

Workup

  1. customPrepared
  2. customdid not rise above 25° C
  3. stirringAfter an additional 18 h of stirring
  4. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-4428fc630e32474da362540f13d1750d
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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