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

HRID 1813924노트

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HRID 1813924 반응식
[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

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178424484HCID 178424484, 화합물

생성물 1

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

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2754cf77a9954bae993d14e1e86f4eb6
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875769B2

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