Sulfuric Acid → HCID 59265941, Verbindung

HRID 1931374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931374
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2(O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 592659571-(6-Chloro-pyridin-3-yl)cyclopentanol

Produkt 1

HCID 59265941HCID 59265941, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1-(6-Chloropyridin-3-yl)cyclopentanol (2.1 g, 10.5 mmol) was treated with acetic acid (12 mL) and sulfuric acid (4 mL) and the mixture heated to reflux for 30 min. After cooling to room temperature, ice and 2 N NaOH (180 mL) was add and the resulting tan precipitate collected by filtration, washed with H2O and dried giving 2-chloro-5-(cyclopent-1-enyl)pyridine (1.66 g, 88%) as a tan solid: mp 59-60° C., LC/MS (ESI) m/z 179, 1H NMR (300 MHz, CDCl3) δ 8.41 (d, 1H, J=2.4 Hz), 7.66 (dd, 1H, J=8.4, 2.4 Hz), 7.25 (d, 1H, J=8.4 Hz), 6.27 (t, 1H, J=2.1 Hz), 2.69 (bm, 2H), 2.55 (bm, 2H), 2.05 (m, 2H).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 min
  3. filtrationthe resulting tan precipitate collected by filtration
  4. washwashed with H2O
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f190c7ad7c5c441b89ac988cfe0393e3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188292B2

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