Dimethylamine → HCID 62302278, compound

HRID 1505171Notes

Reaction equation

HRID 1505171 reaction equation
F[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][NH:12][CH3:13]>>[CH3:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:12]([CH3:13])[CH3:11])[CH:9]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 62302278HCID 62302278, compoundYield 99%

Conditions

Temperature
80 °C

Procedure

To commercially available 2-fluoro-4-methylbenzonitrile 15b (2.5 g, 18.5 mmol) was added dimethylamine (4 equiv., 4.8 ml) and the solution was heated at 80° C. overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 2.96 g of a yellow oil. Yield=99% 1HNMR (DMSO, 200 MHz) δ 2.31 (3H, s), 2.93 (6H, s), 6.74 (1H, dd, J=8 Hz, J′=0.8 Hz), 6.85 (1H, s), 7.47 (1H, d, J=8 Hz)

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with water and brine
  4. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-d2785c303bba4343ae878284b826915a
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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