N-bromobutanimide → 6-Bromo-2,3-dihydro-1H-inden-5-amine

HRID 2259619Notes

Reaction equation

HRID 2259619 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[Br:11]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Br:11])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90496Indan-5-amine

Product 1

HCID 224002746-Bromo-2,3-dihydro-1H-inden-5-amineYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Aminoindan (3.0 g, 22.5 mmol) was dissolved in 10 ml of anhydrous dimethylformamide. A solution of N-bromosuccinimide (4.0 g, 22.5 mmol) in 10 ml anhydrous dimethylformamide was added, and the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between ethyl acetate and water, and the separated organic layer washed twice with H2O, then with brine. Drying over Na2SO4 followed by filtration and evaporation of solvent gave a dark brown oil as the crude product. Purification by flash chromatography (50% EtOAc/hexane) provided 5-amino-6-bromoindan (3.26 g, 68% yield), a compound of Formula 2 where X is bromo, as a brown oil which crystallized into a brown solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe separated organic layer washed twice with H2O
  3. dry with materialDrying over Na2SO4
  4. filtrationfollowed by filtration and evaporation of solvent
  5. customgave a dark brown oil as the crude product
  6. customPurification by flash chromatography (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-b69d7d2917b34a0aad5519eb2153ab5e
Source dataset
uspto-grants-1995_12
Patent number
US05475003

Reaction notes

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