Ethyl orthoformate → 4(3H)-Quinazolinone, 3-(3-bromo-2-methylphenyl)-2-methyl-

HRID 1811012

Reaktionsgleichung

Reaktionsgleichung von HRID 1811012
[CH3:1][C:2]1O[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C(OC(OCC)OCC)C>C1COCC1.C(Cl)Cl>[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([N:17]2[C:4](=[O:12])[C:5]3[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:7]=[C:2]2[CH3:1])[CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 31214Ethyl orthoformateHCID 68236AcetanthranilHCID 1235383-Bromo-o-toluidine

Produkt 1

HCID 633694(3H)-Quinazolinone, 3-(3-bromo-2-methylphenyl)-2-methyl-Ausbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-4H-benzo[d][1,3]oxazin-4-one (300 mg, 1.862 mmol), 3-bromo-2-methylaniline (346 mg, 1.862 mmol), and triethoxymethane (276 mg, 1.862 mmol) in THF (2 mL) was heated overnight in a sealed tube at 100° C. The mixture was cooled to rt and diluted with DCM. The solution was washed with water and NaHCO3 (aq), and dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 50:50 hexane-EtOAc) and the crude product was triturated in hexane to give 3-(3-bromo-2-methylphenyl)-2-methylquinazolin-4(3H)-one as an off-white solid (120 mg, 20%). 1H NMR (400 MHz, chloroform-d) δ 8.28 (1 H, dd, J=7.92, 1.10 Hz), 7.77-7.82 (1 H, m), 7.68-7.73 (2 H, m), 7.47-7.52 (1 H, m), 7.22-7.25 (1 H, m), 7.13-7.17 (1 H, m), 2.20 (6H, s). Mass spectrum m/z 329, 331 (M+H)+.

Aufarbeitung

  1. washThe solution was washed with water and NaHCO3 (aq)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (
  5. washeluting with a gradient from 90:10 to 50:50 hexane-EtOAc) and the crude product
  6. customwas triturated in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f4b029a191074d4d9cb69579b372c9b5
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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