Ammonia methanol → 2-(5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamine

HRID 887795Notes

Reaction equation

HRID 887795 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:14][CH2:13][C:12](=[CH:15][C:16]#[N:17])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2.N.CO>CO.O1CCCC1.[Co]>[Cl:1][C:2]1[C:3]2[CH2:14][CH2:13][C:12](=[CH:15][CH2:16][NH2:17])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2

Participants

6

Reactant 2

HCID 21705897Ammonia methanolHCID 68697773(5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile

Product 1

HCID 686990322-(5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamineYield 100%

Reagents, catalysts & solvents 3

HCID 104730CobaltCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(5-Chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile (116 mg, 2.87 mmol) was dissolved in a mixture of methanol (5 mL) and tetrahydrofuran (5 mL), Raney cobalt (1 g) and 8M ammonia/methanol solution (2 mL) were added to the solution, and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (118 mg, yield 100%).

Workup

  1. additionwere added to the solution
  2. filtrationThe catalyst was filtered off through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-140a997a8c8e4444ade85b276248a7df
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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