N-bromobutanimide → HCID 17972674, compound

HRID 1372533Notes

Reaction equation

HRID 1372533 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([CH2:15][CH3:16])[CH2:8]2)(=[O:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>CN(C)C=O>[C:1]([NH:4][C:5]1[C:6]([Br:17])=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([CH2:15][CH3:16])[CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 202319645-(Acetylamino)-2-ethyl-1-indanone

Product 1

HCID 17972674HCID 17972674, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-(acetylamino)-2-ethyl-1-indanone (2.32 g, 10.7 mmol) in anhydrous N,N-dimethylformamide (10.7 mL) was treated with N-bromosuccinimide (2.00 g, 11.21 mmol). The mixture was placed under a N2 atmosphere, stirred, and heated in an oil bath at 60° C. for 100 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (200 mL) and water (200 mL). The organic phase was washed with water (4×200 mL) and brine (100 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford crude 5-(acetylamino)-4-bromo-2-ethyl-1-indanone as a yellow solid (2.95 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between EtOAc (200 mL) and water (200 mL)
  3. washThe organic phase was washed with water (4×200 mL) and brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-99f2b0b026594200a67e1fd0b3be6da9
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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