Phosphorus oxychloride → 4,8-Dichloro-7-methoxy-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinoline

HRID 407560Notes

Reaction equation

HRID 407560 reaction equation
[Cl:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2O.O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[C:3]([O:21][CH3:22])=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]2[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487693HCID 178487693, compound

Product 1

HCID 579564004,8-Dichloro-7-methoxy-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolineYield 97%

Procedure

A solution of 8-chloro-4-hydroxy-2-(4-isopropylthiazole-2-yl)-7-methoxy-quinoline (2.0 g, 5.97 mmol) in POCl3 (10 mL) was heated at 85° C. during 30 min. Then, the reaction mixture was concentrated under reduced pressure. The residue was poured into ice-cooled water (20 mL), the pH was adjusted to 10 with 50% NaOH, and extracted with CH2Cl2. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to give 2.05 g (97%) of the title compound 92 as a yellow solid: m/z=353 (M+H)+.

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. additionThe residue was poured into ice-
  3. temperaturecooled water (20 mL)
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4d315b3ec2bf40e081f1317e7a1302dd
Source dataset
uspto-grants-2014_06
Patent number
US08754106B2

Reaction notes

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