4-Methoxybenzaldehyde → Indol-2-one

HRID 1441025노트

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HRID 1441025 반응식
COC1C=CC(C=O)=CC=1.Cl[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17](C)[C:16](=[O:22])[CH2:15]2.N1CCCC1>CO>[N:17]1[C:16](=[O:22])[CH:15]=[C:14]2[C:18]=1[CH:19]=[CH:20][CH:12]=[CH:13]2

참가 물질

5

반응물 3

HCID 312444-MethoxybenzaldehydeHCID 31268PyrrolidineHCID 109761125-chloro-1-methyl-2,3-dihydro-1H-indol-2-one

생성물 1

HCID 17904787Indol-2-one수율 11%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

3-(exo-Bicyclo 2.2.1!hept-2-yloxy)-4-methoxybenzaldehyde (677 mg, 2.75 mmol; disclosed in WO 87/06576 published Nov. 5, 1987), and 5-chloro-1-methyloxindole (500 mg, 2.75 mmol; Chemical Abstracts registry number 41192-33-0, were dissolved in 10 ml of methanol under an inert atmosphere. To this brown, homogeneous mixture was added 0.23 ml of pyrrolidine (2.75 mmol) via syringe. The reaction mixture was stirred at room temperature for ten hours. The solvent was then stripped off and the resulting yellow oil was purified via flash chromatography (1:1 ethyl ether/hexane) to provide the desired Z-adduct 3- 3-(bicyclo 2.2.1!hept-2-yloxy)-4-methoxyphenyl!methylene!-5-chloro-1,3-dihydro-1-methyl- 1α,2α(Z),4α!-2H-indol-2-one (125 mg, 11% yield) as a yellow solid (Example 1): m.p. 149°-151°. Analysis calculated for C24H24ClNO3 : C, 70.32; H, 5.90; N, 3.42. Found: C, 70.26; H, 5.87; N, 3.38. The corresponding E-adduct 3- 3-(bicyclo 2.2.1!hept-2-yloxy)-4-methoxyphenyl!methylene!-5-chloro-1,3-dihydro-1-methyl- 1α,2α(E),4α!-2H-indol-2-one (Example 2) was also obtained in 6% yield, m.p. 142°-144° C. Analysis calculated for C24H24ClNO3 : C, 70.32; H, 5.90; N, 3.42. Found: C, 70.34; H, 5.85; N, 3.36.

후처리

  1. customthe resulting yellow oil was purified via flash chromatography (1:1 ethyl ether/hexane)
  2. customto provide the desired Z-adduct 3- 3-(bicyclo 2.2.1

출처 및 근거

ORD 기록
ord-1d9477dc35314ea3a887f3b9b95188d7
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05502072

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