m-Chloroperbenzoic acid → 7-Methylquinoline-2-carbonitrile 1-oxide

HRID 2422534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422534
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:19].[OH-].[Ca+2].[OH-]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[N+:9]([O-:19])[C:8]([C:12]#[N:13])=[CH:7][CH:6]=2

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 107971837-Methylquinoline-2-carbonitrile

Produkt 1

HCID 667907327-Methylquinoline-2-carbonitrile 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-methylquinoline-2-carbonitrile (14.2 g, 84 mmol) in dichloromethane (400 mL) was added 3-chloroperoxybenzoic acid (50%, 36.4 g, 106 mmol) and stirred at room temperature overnight. Solid calcium hydroxide (7.8 g, 106 mmol) was added and 15 min later the mixture was filtered through celite, rinsed with dichloromethane and the liquors evaporated to dryness to give the crude compound. The compound was purified by flash chromatography on silica gel (eluting with 5% acetone in dichloromethane) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.40 (s, 1H), 8.05 (d, 1H), 7.97 (d, 1H), 7.75 (m, 2H), 2.65 (s, 3H).

Aufarbeitung

  1. filtrationwas filtered through celite
  2. washrinsed with dichloromethane
  3. customthe liquors evaporated to dryness
  4. customto give the crude compound
  5. customThe compound was purified by flash chromatography on silica gel (eluting with 5% acetone in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-57f35f98304848da932abdacb368ea8d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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