Chlorosuccinimide → 5-Amino-2-butyl-4-chloro-6-fluoro-2,3-dihydro-1H-inden-1-one

HRID 1372503Notes

Reaction equation

HRID 1372503 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[CH:6]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]2.[Cl:17]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[CH:6]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 179727175-Amino-2-butyl-6-fluoro-1-indanone

Product 1

HCID 210720045-Amino-2-butyl-4-chloro-6-fluoro-2,3-dihydro-1H-inden-1-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-amino-2-butyl-6-fluoro-1-indanone (5.14 g, 23.2 mmol) in N,N-dimethylformamide (23 mL) was placed under a nitrogen atmosphere and treated with N-chlorosuccinimide (3.2 g, 24 mmol). After stirring at room temperature for 3 hours, the reaction mixture was partitioned between EtOAc and water. The organic portion was washed with water and brine, dried over MgSO4, filtered, and evaporated under vacuum to an orange solid (6.5 g). The crude product was purified by flash chromatography on a Biotage 40M KP-Sil column, eluting with 9:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to afford 5-amino-2-butyl-4-chloro-6-fluoro-1-indanone (5.2 g, 88%) as a yellow solid.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and water
  2. washThe organic portion was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum to an orange solid (6.5 g)
  6. customThe crude product was purified by flash chromatography on a Biotage 40M KP-Sil column
  7. washeluting with 9:1 hexanes-EtOAc
  8. additionThe product containing fractions
  9. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-8c106e01044f416a986966d398a56baf
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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