Acetic Acid → HCID 58358306, compound

HRID 446766

Reaction equation

HRID 446766 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:15][CH:14]3[C:16]([NH:18][NH2:19])=[O:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:20]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([CH:30]=O)[C:24]=2[CH:23]=[CH:22][N:21]=1.C(O)(=O)C>C(O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[CH2:15][CH:14]3[C:16]([NH:18]/[N:19]=[CH:30]/[C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:24]=3[CH:23]=[CH:22][N:21]=[CH:20]4)=[O:17])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7016853Isoquinoline-5-carboxaldehydeHCID 583583052-(4-Cyclohexylphenyl)cyclopropanecarbohydrazide

Product 1

HCID 58358306HCID 58358306, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-30f36dbb74014371aea12e360eb5eb25
Source dataset
uspto-grants-2013_07
Patent number
US08481532B2

Linked notes

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