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

HRID 1813924Notes

Reaction equation

HRID 1813924 reaction equation
[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

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424484HCID 178424484, compound

Product 1

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

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2754cf77a9954bae993d14e1e86f4eb6
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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