4-Cyanophenylhydrazine Hydrochloride → 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole-7-carbonitrile

HRID 2427256Notes

Reaction equation

HRID 2427256 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:3]1.Cl.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27]N)=[CH:23][CH:22]=1)#[N:20]>CC(O)=O.O1CCOCC1.Cl.O>[O:17]=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15](=[O:16])[N:7]1[CH:4]1[CH2:5][C:6]2[NH:27][C:24]3[CH:23]=[CH:22][C:21]([C:19]#[N:20])=[CH:26][C:25]=3[C:2]=2[CH2:3]1

Participants

6

Reactant 2

HCID 162129624-Cyanophenylhydrazine HydrochlorideHCID 545940982-(3-Oxocyclopentyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 581494122-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole-7-carbonitrileYield 66.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 204431481,4-Dioxane hydrochlorideSolvent2×

Procedure

Mix (±)-2-(3-oxo-cyclopentyl)-isoindole-1,3-dione (12.7 g, 55.3 mmol) and 4-cyanophenylhydrazine-HCl (8.53 g, 50.3 mmol) in HOAc (200 mL) and 4N HCl dioxane (50 mL). Using mechanical stirring, heat the reaction to 90° C. for 18 h, then add additional 4N HCl dioxane (20 mL). Heat the reaction to 100° C. for 18 h. Dilute the reaction mixture with water (600 mL) and collect a black solid by vacuum filtration. Sonicate the solid with MeOH (200 mL), then collect and dry in a vacuum oven to give 10.94 g (66%) of a gray-brown solid. MS (m/z): 328 (M+1), 326 (M−1).

Workup

  1. temperatureheat
  2. customthe reaction to 90° C. for 18 h
  3. temperatureHeat
  4. customthe reaction to 100° C. for 18 h
  5. customcollect a black solid
  6. filtrationby vacuum filtration
  7. customSonicate the solid with MeOH (200 mL)
  8. customcollect
  9. customdry in a vacuum oven

Sources & evidence

ORD record
ord-dc192e3eb52544b485b24427724f5a45
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

Loading…