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

HRID 1954926Notes

Reaction equation

HRID 1954926 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 37.6%

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 watts (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 7.52 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-0a87bfb7497d4cad9b5c5f7586173bf0
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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