Potassium Carbonate → 4-Cyclopropylamino-nicotinonitrile

HRID 2264947Notes

Reaction equation

HRID 2264947 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]#[N:9].[CH:10]1([NH2:13])[CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH:10]1([NH:13][C:2]2[C:3]([C:8]#[N:9])=[CH:4][N:5]=[CH:6][CH:7]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 134111124-Chloro-nicotinonitrile

Product 1

HCID 595964594-Cyclopropylamino-nicotinonitrileYield 79.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-chloro-3-cyanopyridine (5.0 g, 36.1 mmol), cyclopropylamine (5.0 mL, 72.2 mmol, 2.0 eq), and potassium carbonate (5.2 g, 37.9 mmol, 1.05 eq) in isopropyl alcohol (130 mL) was stirred at 60° C. under N2 for 20 h. The reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was absorbed onto silica and purified by flash column chromatography (silica, ISCO, 45 mL/min, 10-100% ethyl acetate in hexane). Trituration from hexane afforded the title compound as an off-white solid (4.55 g, 79.3%). 1H-NMR (400 MHz; DMSO-d6) δ ppm 8.43 (d, J=0.55 Hz, 1H), 8.29 (dd, J=6.10 Hz, 1H), 7.55 (s, 1H), 7.00-6.88 (m, 1H), 2.54 to 2.40 (m, 1H), 0.89-0.69 (m, 2H), 0.68-0.48 (m, 2H); LC-MS (method C): [M+H]+=160.2, RT=0.28 min.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was absorbed onto silica
  4. custompurified by flash column chromatography (silica, ISCO, 45 mL/min, 10-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c02725f057e14383a139c7c879bec939
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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