N-bromobutanimide → 6-Amino-7-bromo-2,3-dihydro-1H-inden-1-one

HRID 1947772Notes

Reaction equation

HRID 1947772 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:10]([Br:12])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3128956-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 534220646-Amino-7-bromo-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-aminoindanone (12 g, 81.6 mmol) in N,N-dimethylformamide (220 ml) is treated with N-bromosuccinimide (14.5 g, 81.6 mmol) in portions over a period of one hour and stirred for one hour. Evaporation of the solvent and water/dichloromethane workup followed by purification by chromatography with EtOAc/hexane (1:3) as eluent gives the product 6-amino-7-bromoindanone; LC/MS: 226/228 (M+1)+.

Workup

  1. customEvaporation of the solvent and water/dichloromethane workup
  2. customfollowed by purification by chromatography with EtOAc/hexane (1:3) as eluent

Sources & evidence

ORD record
ord-081e82fd7d164541803bba57ef91a2d7
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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