3-(3-Methylbutanamido)isonicotinic acid → 2-isobutyl-4H-pyrido[3,4-d][1,3]oxazin-4-one

HRID 1867457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867457
[CH3:1][CH:2]([CH3:16])[CH2:3][C:4]([NH:6][C:7]1[CH:15]=[N:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=O>C(OC(=O)C)(=O)C>[CH2:3]([C:4]1[O:10][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][N:14]=[CH:15][C:7]=2[N:6]=1)[CH:2]([CH3:16])[CH3:1]

Komponenten

3

Edukt 1

HCID 643935913-(3-Methylbutanamido)isonicotinic acid

Produkt 1

HCID 221726032-isobutyl-4H-pyrido[3,4-d][1,3]oxazin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

To 3-[(3-methylbutanoyl)amino]isonicotinic acid (3.30 g, 14.84 mmol) was added acetic anhydride (20 mL, 0.78M) and the reaction was heated to 125° C. with a short path distillation head. The reaction was heated for 2 h and then cooled to room temperature. Excess acetic anhydride was then removed by vacuum distillation (20 Torr, 70° C.). The residue was cooled to room temperature and azeotroped twice with toluene to provide the title compound as a tan oil. 1H NMR (500 MHz, CDCl3) δ 1.06 (d, J=6.5 Hz, 6H), 2.31-2.35 (m, 1H), 2.61 (d, J=7 Hz, 2H), 7.96 (d, J=5 Hz, 1H), 8.78 (d, J=4.5 Hz, 1H), 9.03 (s, 1H). MS [M+H] C11H12N2O2=205.3

Aufarbeitung

  1. temperatureThe reaction was heated for 2 h
  2. temperaturecooled to room temperature
  3. customExcess acetic anhydride was then removed by vacuum distillation (20 Torr, 70° C.)
  4. temperatureThe residue was cooled to room temperature
  5. customazeotroped twice with toluene

Quellen und Nachweise

ORD-Eintrag
ord-2a96e2ff15674a01a342045329417ad8
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632839B2

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