Hydrochloric Acid → 5-Chloro-3-hydroxy-3-(2-methoxy-6-methylphenyl)-1,3-dihydro-2H-indol-2-one

HRID 31351

반응식

HRID 31351 반응식
[Mg:1].[Br:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[O:10][CH3:11].[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[C:16]2=[O:23].Cl.C1[CH2:29][O:28]CC1>>[CH3:29][O:28][C:13]1[CH:21]=[CH:20][CH:19]=[C:15]([CH3:16])[C:14]=1[Mg:1][Br:2].[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[C:16]2([OH:23])[C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[O:10][CH3:11]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran3회HCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224MagnesiumHCID 117902332-Bromo-3-methoxytoluene

생성물 2

HCID 225609215-Chloro-3-hydroxy-3-(2-methoxy-6-methylphenyl)-1,3-dihydro-2H-indol-2-oneHCID 178489966HCID 178489966, 화합물

실험 절차

A solution of 2-methoxy-6-methylphenyl-magnesium bromide is prepared starting with 2.2 g of magnesium in 10 ml of THF and a solution of 16 g of 1-bromo-2-methoxy-6-methylbenzene in 40 ml of THF. This solution is added dropwise at RT to a mixture of 6 g of 5-chloro-1H-indole-2,3-dione in 50 ml of THF and the resulting mixture is then refluxed for 1 hour. After cooling to RT, the reaction mixture is poured into 200 ml of 3N HCl solution and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 5.7 g of the expected product are obtained after crystallization from iso ether.

후처리

  1. temperaturethe resulting mixture is then refluxed for 1 hour
  2. extractionextracted with EtOAc
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

출처 및 근거

ORD 기록
ord-17e7d9b1df4c454297e9cd3442b4d85f
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425566B2

연결된 노트

불러오는 중…