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m-Chloroperbenzoic acid → 8-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolin

HRID 598309
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인쇄 미리보기

반응식

HRID 598309 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:20]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[N:21]([CH3:22])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:36]C1C=CC2C3N(CC(C)C)C(C)=NC=3C=NC=2C=1)C1C=CC=CC=1.C1C=C(Cl)C=C(C(OO)=O)C=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-:36])=[CH:14][C:13]3[N:19]=[C:20]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[N:21]([CH3:22])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 670509187-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolineHCID 670510438-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 670510018-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolin

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

A modification of the general method described in Part B of Example 3 was followed using 8-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-1H-imidazo[4,5-c]quinoline (5.4 g, 14 mmol) in lieu of 7-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline. Dichloromethane (100 mL) was used as the solvent, and after three hours an analysis by TLC indicated the reaction was incomplete. Additional mCPBA (0.5 equivalents) was added, and the reaction was terminated after one additional hour. After the work-up the product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol to provide 1.5 g of 8-benzyloxy-2-[2-methoxy(ethoxymethyl)]-1-methyl-5-oxido-1H-imidazo[4,5-c]quinolin as an oil.

후처리

  1. customthe reaction was terminated after one additional hour
  2. customAfter the work-up the product was purified by column chromatography on silica gel (
  3. washeluting with 90:10 dichloromethane

출처 및 근거

ORD 기록
ord-47ff538f018042bca996f91bfc4627ce
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07897597B2

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