Methanol → (E)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamide

HRID 862771Notes

Reaction equation

HRID 862771 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([OH:15])/[C:8]/2=[CH:11]\[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1.CO>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([OH:15])/[C:8]/2=[CH:11]/[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 15491031(Z)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamide

Product 1

HCID 23293575(E)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamideYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (Z)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamide (5.456 g, 0.026 mol) in dichloromethane:methanol/9:1 (1000 ml) was irradiated by an Canrad-Hanovia quartz, mecury-vapor photochemical immersion lamp, 450 wattts (Ace Glass, 7825-35) for 1h. The volitiles were removed by spin evaporation in vacuo to give a light brown solid 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 (E)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamide were combined and concentrated by spin evaporation in vacuo. The resulting residue was recrystallized from ethanol-hexanes to give 1.31 g (24%) of (E)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamide as an off-white crystalline solid, m.p., 159°-163° C., NMR(DMSO-d6): d 8.56 (dd, 1H, JHF =11.0 Hz, JHH =2.9 Hz), 7.67 (br s, 1H), 7.34-7.30 (m, 1H), 7.2-7.13 (m, 1H), 7.06 (br s, 1H),6.18 (s, 1H), 5.69 (d, 1H, J=6.8 Hz), 4.74 (q, 1H, J=12.1 Hz, J=6.0 Hz), 3.21-3.13 (m, 1H) 2.73-2.66(m, 1H); steady state nOe: irradiation at d6.19, observed 5.4% nOe at d4.74, 4.3% at d7.67 and 1.5% at d 5.69.

Workup

  1. customThe volitiles were removed by spin evaporation in vacuo
  2. customto give a light brown solid residue
  3. customThis residue was chromatographed on Silica Gel 60 using a step gradient
  4. additionFractions containing (E)-2-(6-fluoro-2-hydroxy-1-indanylidene)acetamide
  5. concentrationconcentrated by spin evaporation in vacuo
  6. customThe resulting residue was recrystallized from ethanol-hexanes

Sources & evidence

ORD record
ord-ed8d750629d74e3da4a9ef7352f559db
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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