2-Bromo-2-methyl-N-phenylpropanamide → 3,3-Dimethyl-1,3-dihydro-indol-2-one

HRID 620016Notes

Reaction equation

HRID 620016 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([NH:11][C:12](=[O:17])[C:13](Br)([CH3:15])[CH3:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[CH3:14][C:13]1([CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:11][C:12]1=[O:17]

Participants

3

Reactant 2

HCID 948352-Bromo-2-methyl-N-phenylpropanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Procedure

A neat mixture of AlCl3 (8.28 g) and the amide obtained in Step 1. above (5 g) is heated slowly to about 135°-140° C. and maintained at this temperature for about 10-15 min. Ice water is added slowly to the reaction mixture and the residue is extracted with ether. The organic extract is washed with 1N HCl, 10% aqueous sodium carbonate, dried, filtered and evaporated affording a solid. The solid is purified by flash chromatography (silica gel; 2% methanol/methylene chloride) affording the desired product as a white crystalline solid, M.P.=151°-152° C.

Workup

  1. temperatureabove (5 g) is heated slowly to about 135°-140° C.
  2. temperaturemaintained at this temperature for about 10-15 min
  3. extractionthe residue is extracted with ether
  4. extractionThe organic extract
  5. washis washed with 1N HCl, 10% aqueous sodium carbonate
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customaffording a solid
  10. customThe solid is purified by flash chromatography (silica gel; 2% methanol/methylene chloride)

Sources & evidence

ORD record
ord-fb4495ba630843a1807667fe14629bae
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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