Isoamyl Nitrite → HCID 67084010, Verbindung

HRID 79007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79007
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH3:11])[C:5]=1[Cl:12].C(O[N:20]=O)CC(C)C>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([Cl:12])=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][N:20]=[CH:11]2)=[O:13]

Komponenten

4

Edukt 2

HCID 8053Isoamyl NitriteHCID 67083635HCID 67083635, Verbindung

Produkt 1

HCID 67084010HCID 67084010, VerbindungAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-2-chloro-3-methyl-benzoic acid methyl ester (5.29 g, 26.5 mmol) in acetic acid (100 mL) was added isoamylnitrite (3.9 mL, 29.2 mmol). The reaction mixture was stirred at room temperature for 30 minutes then heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, gradient 0-100% ethyl acetate in cyclohexane) to yield the title compound as an off-white solid (2.26 g, 40%). 1H NMR (CDCl3, 400 MHz) 3.97 (3H, s), 7.42 (1H, d, J=8.8 Hz), 7.95 (1H, d, J=8.8 Hz), 8.29 (1H, s).

Aufarbeitung

  1. temperaturethen heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72a07da25f844ac1b0aaad77fd82bccd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841462B2

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