Phosphorus oxychloride → 2-Methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline

HRID 1813924ノート

反応式

HRID 1813924 の反応式
[CH3:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[C:5]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:10]1[C:9]2[C:4](=[C:5]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178424484HCID 178424484、化合物

生成物 1

HCID 225043522-Methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline収率 87%

反応条件

温度
130 °C

実験手順

A mixture of 2-methyl-8-(2,4,6-trimethyl-phenyl)-quinolin-4-ol(335 mg, 1.21 mmol) and POCl3(2.5 ml) was heated in 130° C. oil bath for 3 hours. The mixture was cooled and poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 350 mg of crude material as a brown oil. The oil residue was purified through silica gel column chromatography using chloroform as eluent to give 316 mg (87%) of the title compound as a yellow oil. 1H NMR (CDCl3) δ 8.20(d,1H), 7.60(m,1H), 7.47(d,1H), 7.35(s,1H), 6.97(s,2H), 2.54(s,3H), 2.36(s,3H), 1.86(s,6H)ppm.

後処理

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give 350 mg of crude material as a brown oil
  7. customThe oil residue was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-2754cf77a9954bae993d14e1e86f4eb6
出典データセット
uspto-grants-2005_04
特許番号
US06875769B2

反応ノート

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