Phosphorus oxychloride → 4-Chloro-7-methylquinoline-2-carbonitrile

HRID 2422535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422535
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[N+:9]([O-])[C:8]([C:13]#[N:14])=[CH:7][CH:6]=2.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:13]#[N:14])[CH:7]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 667907327-Methylquinoline-2-carbonitrile 1-oxide

Produkt 1

HCID 597749194-Chloro-7-methylquinoline-2-carbonitrile

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 7-methylquinoline-2-carbonitrile 1-oxide (11.5 g, 63 mmol) and phosphorus oxychloride (47 mL, 500 mmol) was heated at 100° C. for 10 min then at 200° C. for 20 min. The reaction mixture was poured into crushed ice and the precipitate was filtered. The crude material was then purified by flash chromatography on silica gel (eluting solvent: 3% acetone in dichloromethane) to provide the title compound. 1HNMR (400 MHz, acetone-d6): δ 8.25 (d, 1H), 8.10 (s, 1H), 8.00 (d, 1H), 7.82 (dd, 1H), 2.65 (s, 3H).

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. filtrationthe precipitate was filtered
  4. customThe crude material was then purified by flash chromatography on silica gel (eluting solvent: 3% acetone in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-214f58c58b894c908e413bc793447d6b
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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