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

HRID 883202Notes

Reaction equation

HRID 883202 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[CH:14][C:15]#[N:16])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.N.C(O)C>C(O)C.[Co]>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[CH:14][CH2:15][NH2:16])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 67353411(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile

Product 1

HCID 673538152-(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethanamine

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile (290 mg, 1.38 mmol) in ethanol (8 mL) were added Raney cobalt (3 g) and 2N ammonia/ethanol solution (4 mL), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere. The catalyst was filtered off using celite, and the filtrate was concentrated under reduced pressure to give the title compound. The obtained title compound was used for the reaction of Examples 3 and 5 without further purification.

Workup

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

Sources & evidence

ORD record
ord-6c9e984bfe9d4c9589cc1fbc175a5cbe
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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