Ethanol, reaction products with ammonia, distn. residues → 3-(2-Aminoethylidene)-4-methoxyindan-5-amine

HRID 340684Notes

Reaction equation

HRID 340684 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[CH:13][C:14]#[N:15])=[CH:4][CH:3]=1.N.C(O)C>C(O)C.[Co]>[NH2:15][CH2:14][CH:13]=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH2:1])[C:10]=2[O:11][CH3:12])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 67353001(6-Amino-7-methoxy-2,3-dihydro-1H-inden-1-ylidene)acetonitrile

Product 1

HCID 673546943-(2-Aminoethylidene)-4-methoxyindan-5-amineYield 99%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (6-amino-7-methoxy-2,3-dihydro-1H-inden-1-ylidene)acetonitrile (15.2 mg, 0.076 mmol) in ethanol (0.5 mL) were added Raney cobalt (150 mg) and 2N ammonia/ethanol solution (0.5 mL), and the mixture was stirred at room temperature for 2 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 (15.3 mg, yield 99%).

Workup

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

Sources & evidence

ORD record
ord-f8f1b9f725824b6ab487ddb15e927376
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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