Ethanol, reaction products with ammonia, distn. residues → 2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamine

HRID 887764Notes

Reaction equation

HRID 887764 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[N:16])[C:8]=32)=[N:3]1.N.C(O)C>C(O)C.[Co]>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][NH2:16])[C:8]=32)=[N:3]1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 68699579(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile

Product 1

HCID 686989692-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamineYield 100.3%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile (600 mg, 2.87 mmol) in ethanol (14 mL) were added Raney cobalt (6 g) and 2M ammonia/ethanol solution (14 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (614 mg, yield 99%).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b2f92781b614cb98c0dd3b6eafc81ce
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

Loading…