Acetone → 5-fluoro-2,3-dihydro-1H-isoindole hydrochloride

HRID 268710Notes

Reaction equation

HRID 268710 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:17])[CH:14]=2)[CH2:9]1)C1C=CC=CC=1.[H][H].CC(C)=O.[ClH:24]>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:24].[F:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:16]2

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 179862982-Benzyl-5-fluoroisoindolineHCID 178418361HCID 178418361, compound

Product 1

HCID 179862865-fluoro-2,3-dihydro-1H-isoindole hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 20% palladium hydroxide on carbon (4.0 g) and N-benzyl-5-fluoroisoindoline (D7) (44.6 g) in ethanol (475 ml) and conc. hydrochloric acid (d=1.18, 25 ml) was stirred with hydrogen at 50 psi for 18 h at 45° C. The mixture was cooled to ambient temperature and filtered to remove the catalyst. The filtrate was evaporated in vacuo to give a solid which was stirred with acetone (300 ml) for 0.5 h and filtered to give the title compound (D8) as a solid (29.3 g). 1H NMR δ (D6-DMSO): 10.0 (2H, br, s), 7.41-7.46 (1H, m), 7.15-7.29 (2H, m), 4.49 (2H, s), 4.46 (2H, s).

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. customThe filtrate was evaporated in vacuo
  4. customto give a solid which
  5. filtrationfiltered

Sources & evidence

ORD record
ord-20c799033ff34158b00b72bc5a4ca4e5
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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