Ethanol, reaction products with ammonia, distn. residues → HCID 21996512, compound

HRID 1977984Notes

Reaction equation

HRID 1977984 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.[Co]>[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

Participants

5

Reactant 2

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

Product 1

HCID 21996512HCID 21996512, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1,2,3,4-tetrahydro-7-methoxy-1-naphthylidene)acetonitrile (4.0 g, 20 mmol) in ethanol (10 ml) were added a saturated ammonia/ethanol solution (5 ml) and Raney cobalt (ODHT-60, 1 g). The reaction mixture was stirred for 3.5 hours at room temperature under hydrogen atmosphere (about 4 kgf/cm2). The Raney cobalt was filtered off, then the solvent was distilled off under reduced pressure. To the residue was added dilute hydrochloric acid, then the organic layer was subjected to extraction with ethyl acetate. The extract solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography to give the above-titled compound (yield 2.14 g, oil).

Workup

  1. filtrationThe Raney cobalt was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue was added dilute hydrochloric acid
  4. extractionthe organic layer was subjected to extraction with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, which
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-31d3ae4f705a461cacd3bfd4b17bbbba
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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