Ammonium formate → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

HRID 2383369Notes

Reaction equation

HRID 2383369 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:6][CH:5]=1.C([O-])=O.[NH4+]>C(O)C.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]2=[O:21])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

Product 1

HCID 591459612-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-{2-[4-(2-Hydroxy-ethyl)-phenyl]-vinyl}-isoindole-1,3-dione (Preparation 9, 10 g) in ethanol and ethyl acetate (350 mL each) was added 30% palladium hydroxide on carbon (1.44 g) followed by ammonium formate (21.5 g). The reaction was heated to 80° C. for 4 hours. Additional palladium hydroxide on carbon (1.44 g) and ammonium formate (21.5 g) were added and the reaction was stirred at 80° C. for 18 hours. The reaction was cooled, filtered through a pad of Arbocel® and rinsed with methanol. The solvent was removed under reduced pressure and the resulting white solid was partitioned between dichloromethane (200 ml) and water (100 ml). The aqueous layer was separated and extracted with further dichloromethane (2×50 mL). The combined organic layers were dried (sodium sulphate) and the solvent removed in vacuo to give the title compound as an off-white solid, 9.11 g.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a pad of Arbocel®
  3. washrinsed with methanol
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting white solid was partitioned between dichloromethane (200 ml) and water (100 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted with further dichloromethane (2×50 mL)
  8. dry with materialThe combined organic layers were dried (sodium sulphate)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c06ddca49df84140a8c9b8ce0816efed
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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