Bromine → N-(5-acetylamino-6-bromo-indan-2-yl)acetamide

HRID 863493Notes

Reaction equation

HRID 863493 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([NH:14][C:15](=[O:17])[CH3:16])[CH2:8]2)(=[O:3])[CH3:2].[Br:18]Br>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:18])[CH2:10][CH:9]([NH:14][C:15](=[O:17])[CH3:16])[CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 19696254N-(5-acetylamino-indan-2-yl)-acetamide

Product 1

HCID 19696168N-(5-acetylamino-6-bromo-indan-2-yl)acetamideYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(5-acetylamino-indan-2-yl)-acetamide (9.8 g, 42 mmol) and bromine (8.5 g, 53 mmol) in acetic acid (200 mL) was stirred at room temperature for 3 h. After evaporation of the solvent, the syrupy residue was dissolved in ether and washed with water. The organic layer was washed with aqueous sodium bisulfite and dried over magnesium sulfate. The solvent was concentrated and the resulting solid collected by filtration (10 g, 77% yield).

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe syrupy residue was dissolved in ether
  3. washwashed with water
  4. washThe organic layer was washed with aqueous sodium bisulfite
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated
  7. filtrationthe resulting solid collected by filtration (10 g, 77% yield)

Sources & evidence

ORD record
ord-021d9269f5a9443ba7e198ae3b6dd52c
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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