N,N-Dimethylethylenediamine → HCID 28375983, compound

HRID 748501Notes

Reaction equation

HRID 748501 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH2:15]>CN(C)C=O>[NH3:10].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:15][CH2:14][CH2:13][N:12]([CH3:16])[CH3:11])=[O:7]

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 2369852-Chloroisonicotinic acid

Product 2

HCID 222AmmoniaHCID 28375983HCID 28375983, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloroisonicotinic acid (0.50 g, 3.17 mmol) in N,N-dimethylformamide (20 mL) was added 1,1′-carbonyldiimtidazole (0.565 g, 3.49 mmol). The solution was heated at 70° C. for 30 min. The reaction mixture was cooled to room temperature and N,N-dimethylethane-1,2-diamine (0.31 g, 3.49 mmol) was added. The solution was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue was purified on a silica gel column using chloroform/methanol/conc. NH3(aq), (90:10:1), as the eluent to afford 40 mg (5,7% yield) of the title compound as a colorless oil: 1H NMR (CDCl3, 400 MHz) 8.51 (d, J=5 Hz, 1 H), 7.68 (s, 1 H), 7.56 (dd, J=5, 1 Hz, 1 H), 6.92-7.08 (br s, 1 H), 3.58-3.48 (m, 2 H), 2.59-2.52 (m, 2 H), 2.28 (s, 6 H); MS (TSP) m/z 228 (M++1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-f842194ece9945569491c295b541ea3b
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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