Acetic Acid → 2-(4-cyclohexylphenyl)-N-[(E)-isoquinolin-5-ylmethylideneamino]cyclopropane-1-carboxamide

Temperature

80 °C

To a room temperature solution of 2-(4-cyclohexylphenyl)cyclopropanecarbohydrazide (200 mg) in ethanol (20 mL), was added isoquinoline-5-carbaldehyde (122 mg, 0.77 mmol) and acetic acid (0.5 mL). The reaction mixture was then heated at 80° C. for 3 h, concentrated in vacuo and the residue diluted with water and extracted with EtOAc (2×20 mL). The layers were separated and then the combined organic layers were washed with a saturated NaHCO3 solution, dried over magnesium sulfate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via column chromatography eluting with 2% MeOH in dichloromethane to afford (E)-2-(4-cyclohexylphenyl)-N′-(isoquinolin-5-ylmethylene)cyclopropanecarbohydrazide (100 mg, 33%) as a white solid.

1. concentrationconcentrated in vacuo
2. additionthe residue diluted with water
3. extractionextracted with EtOAc (2×20 mL)
4. customThe layers were separated
5. washthe combined organic layers were washed with a saturated NaHCO3 solution
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto obtain the crude product
10. customThe crude material was purified via column chromatography
11. washeluting with 2% MeOH in dichloromethane

ORD record

ord-30f36dbb74014371aea12e360eb5eb25

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481532B2