Trifluoroacetic acid → 6-Methoxy-2,3-dihydro-1H-isoindol-1-one

HRID 1761022Notes

Reaction equation

HRID 1761022 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8](CC3C=CC(OC)=CC=3)[C:9]2=[O:12])=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O.S(O)(C(F)(F)F)(=O)=O.C(=O)([O-])O.[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 114375476-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-one

Product 1

HCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-oneYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Alternatively, a mixture of 6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (98.5 mg, 0.35 mmol) in dichlormethane (10 mL) containing TFA (1.6 mL, 20.8 mmol) and TfOH (0.6 mL, 7.0 mmol) was heated overnight at 40° C. Then the mixture was poured into sodium hydrogen carbonate and water and the product extracted with dichloromethane. The combined organic layers were then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1) to afford the title product (24 mg, 42%) as a light yellow solid. MS m/e=164.2 (M).

Workup

  1. extractionthe product extracted with dichloromethane
  2. dry with materialThe combined organic layers were then dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1)

Sources & evidence

ORD record
ord-6649b023f8594aafb07cd2645c2f598a
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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