(E)-(6-methoxyindan-1-ylidene)acetonitrile → (E)-1-(2-Aminoethylidene)-6-methoxyindan

HRID 582201Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[CH:12]\[C:13]#[N:14])=[CH:5][CH:4]=1.N.CO>C(O)C.[Co]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[CH:12]\[CH2:13][NH2:14])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (E)-(6-methoxyindan-1-ylidene)acetonitrile (1.60 g, 8.64 mmol.) in ethanol (80 ml) were added a 2M ammonia/methanol solution (40 ml) and Raney cobalt (1.6 g). The reaction mixture was stirred, under hydrogen atmosphere (4 kgf/cm2) for 32 hours at 40° C. and for further 8 hours at 70° C. The Raney cobalt was filtered off, and then the solvent was distilled off. The residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1 to chloroform:methanol:triethylamine=90:8:2) to afford the titled compound (1.40 g, yield 86%, oily).

Workup

waitfor further 8 hours at 70° C
filtrationThe Raney cobalt was filtered off
distillationthe solvent was distilled off
customThe residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1 to chloroform:methanol:triethylamine=90:8:2)

Sources & evidence

ORD record: ord-f082034c6aad4a69bf1d1e2e999859cd
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922771

Reaction notes

Loading…