Peracetic Acid → 7-(Methoxycarbonyl)quinoline 1-oxide

HRID 537191

반응식

HRID 537191 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(OO)(=[O:17])C>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:14][O:13][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N+:1]2[O-:17])=[CH:6][CH:7]=1)=[O:12]

참가 물질

5

반응물 2

HCID 6585Peracetic Acid2회HCID 12554532Methyl quinoline-7-carboxylate

생성물 1

HCID 674916957-(Methoxycarbonyl)quinoline 1-oxide수율 90.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of methyl quinoline-7-carboxylate (17.8 g, 94.87 mmol) in dichloromethane (315 mL) was added peracetic acid (39.9 mL, 190 mmol, 32% in acetic acid). The reaction was stirred at room temperature overnight. Peracetic acid (10 mL, 48 mmol, 32% in acetic acid) was added and the mixture was stirred for 5 h. The reaction mixture was diluted with a saturated solution of aqueous sodium bicarbonate. The aqueous phase was extracted into dichloromethane (2×μL). The extracts were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography (2-15% methanol in dichloromethane) gave the title compound (17.4 g, 90%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d, δ): 9.41 (1H, s), 8.56 (1H, dd, J=6.0, 0.8 Hz), 8.24 (1H, dd, J=8.5, 1.7 Hz), 7.93 (1H, d, J=8.6 Hz), 7.75 (1H, d, J=8.6 Hz), 7.39 (1H, dd, J=8.6, 6.0 Hz), 4.01 (3H, s)

후처리

  1. stirringthe mixture was stirred for 5 h
  2. extractionThe aqueous phase was extracted into dichloromethane (2×μL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (2-15% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-8047b039469c4005a0e15e86a23bf606
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859773B2

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