(E)-2-(6-fluoro-1-indanylidene)acetamide → (Z)-2-(6-fluoro-1-indanylidene)acetamide

HRID 362879Notes

Reaction equation

HRID 362879 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]\[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1>ClCCl.CO.[Hg]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]/[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 9837001(E)-2-(6-fluoro-1-indanylidene)acetamide

Product 1

HCID 11116858(Z)-2-(6-fluoro-1-indanylidene)acetamideYield 37%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of (E)-2-(6-fluoro-1-indanylidene)acetamide (20 g,104.6 mmol) in dichloromethane:methanol(3:1) (1000 ml) was irradiated by an Canrad-Hanovia quartz, mercury-vapor photochemical immersion lamp, 450 wattts (Ace Glass, 7825-35) for 0.5 h. The volatiles were removed by spin evaporation in vacuo to give a beige residue. This residue was chromatographed on Silica Gel 60 using a step gradient going from ethyl acetate: hexanes(1:1) to ethyl acetate:ethanol(1:1). Fractions containing (Z)-2-(6-fluoro-1-indanylidene)acetamide were combined and concentrated by spin evaporation in vacuo. The resulting solid was slurried in hexanes to give 7.2 g (37%) of (Z)-2-(6-fluoro-1-indanylidene)acetamide as a white crystalline solid, m.p.,175°-177 ° C.;

Workup

  1. customThe volatiles were removed by spin evaporation in vacuo
  2. customto give a beige residue
  3. customThis residue was chromatographed on Silica Gel 60 using a step gradient
  4. additionFractions containing (Z)-2-(6-fluoro-1-indanylidene)acetamide
  5. concentrationconcentrated by spin evaporation in vacuo

Sources & evidence

ORD record
ord-9f77df6917cf4f368b62e21f32da9bd3
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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