Ethanol, reaction products with ammonia, distn. residues → 2-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propan-1-amine

HRID 2389927Notes

Reaction equation

HRID 2389927 reaction equation
[CH2:1]([C:3]1[C:14]([CH:15]([CH3:18])[C:16]#[N:17])=[C:6]2[C:7]3[CH2:13][CH2:12][O:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].N.C(O)C>[Co]>[CH2:1]([C:3]1[C:14]([CH:15]([CH3:18])[CH2:16][NH2:17])=[C:6]2[C:7]3[CH2:13][CH2:12][O:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 591793972-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propanenitrile

Product 1

HCID 591793732-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propan-1-amineYield 98.3%

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

A mixture of 2-(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propanenitrile (185 mg, 0.767 mmol), Raney cobalt (1.9 g) and 2M ammonia/ethanol solution (15 mL) was stirred at room temperature for 12 hr under a hydrogen atmosphere, and further stirred at 40° C. for 3 hr. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure to give the title compound (185 mg, yield 98%).

Workup

  1. stirringfurther stirred at 40° C. for 3 hr
  2. filtrationThe catalyst was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2216ee4386e45f8b1329d4b65f29dcf
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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