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

HRID 880949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 880949
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(OO)(=[O:18])C>ClCCl>[CH2:14]([O:13][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N+:1]2[O-:18])=[CH:6][CH:7]=1)=[O:12])[CH3:15]

Komponenten

4

Edukt 2

HCID 6585Peracetic AcidHCID 3799493Ethyl Quinoline-7-carboxylate

Produkt 1

HCID 674915557-(Ethoxycarbonyl)quinoline 1-oxideAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl quinoline-7-carboxylate (1.02 g, 5.05 mmol) in dichloromethane (20 mL) was added peracetic acid (2.13 mL, 10.1 mmol, 32 wt % in acetic acid). The reaction was stirred at room temperature overnight. The reaction was partitioned between water and dichloromethane. The layers were separated and the aqueous was extracted with dichloromethane (4×). The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The solid was concentrated from heptanes and ethyl acetate several times, then dried under vacuum to give the title compound (1.01 g, 92%) as a yellow solid. +ESI (M+H) 218.2; 1H NMR (400 MHz, CDCl3, δ): 9.40 (s, 1H), 8.65 (d, J=6.05 Hz, 1H), 8.27 (dd, J=8.58, 1.56 Hz, 1H), 7.95 (d, J=8.39 Hz, 1H), 7.82 (d, J=8.58 Hz, 1H), 7.42 (dd, J=8.49, 6.15 Hz, 1H), 4.47 (q, J=7.02 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. customThe reaction was partitioned between water and dichloromethane
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with dichloromethane (4×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe solid was concentrated from heptanes and ethyl acetate several times
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5659ecf08f5f4e9683fb55df0f4fb7c6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993586B2

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