Ethanol, reaction products with ammonia, distn. residues → HCID 54094556, compound

HRID 1977985Notes

Reaction equation

HRID 1977985 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[CH:13][C:14]#[N:15])=[CH:5][CH:4]=1.N.C(O)C>C(O)C.[Ni]>[NH2:15][CH2:14][CH:13]=[C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 54328648HCID 54328648, compound

Product 1

HCID 54094556HCID 54094556, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (1,2,3,4-tetrahydro-7-methoxy-1-naphthylidene)acetonitrile (15.0 g, 25 mmol) in ethanol (100 ml) were added a saturated ammonia/ethanol solution (30 ml) and Raney nickel (W-2, 3 g). The reaction mixture was stirred for 8 hours at 50° C. under hydrogen atmosphere (3-4 kgf /cm2). The Raney nickel was filtered off, then the solvent was distilled off under reduced pressure to give the above-titled compound (a mixture of isomers (20.4 g, yield 80%, oil). This compound was used in the subsequent reaction without further purification.

Workup

  1. filtrationThe Raney nickel was filtered off
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9ed2a8b2b3be43028dc7b94878229e42
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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