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

반응식

[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]

참가 물질

반응물 2

HCID 948352-Bromo-2-methyl-N-phenylpropanamide

HCID 6451240Aluminum(III) Chloride

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-fb4495ba630843a1807667fe14629bae
출처 데이터셋: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04818755

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