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

HRID 1811012

反応式

HRID 1811012 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f4b029a191074d4d9cb69579b372c9b5
出典データセット
uspto-grants-2013_01
特許番号
US08362065B2

関連ノート

読み込み中…