Ethanol, reaction products with ammonia, distn. residues → 2-(6,7-Dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethanamine

HRID 340677Notes

Reaction equation

HRID 340677 reaction equation
[O:1]1[C:5]2[C:6]3[C:7](=[CH:13][C:14]#[N:15])[CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][C:4]=2[N:3]=[CH:2]1.N.C(O)C>C(O)C.[Co]>[O:1]1[C:5]2[C:6]3[C:7](=[CH:13][CH2:14][NH2:15])[CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 67353458(6,7-Dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile

Product 1

HCID 673539192-(6,7-Dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethanamineYield 28.1%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile (210 mg, 1.07 mmol) in ethanol (8 mL) were added Raney cobalt (2 g) and 2N ammonia/ethanol solution (4 mL), and the mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere. The catalyst was filtered off using celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0) to give the title compound (60.2 mg, yield 28%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0)

Sources & evidence

ORD record
ord-f34a65798a74444caec865e5505a02e4
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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