Sodium Hydroxide → 2-(4-Chloro-7-methoxy-8-methylquinolin-2-yl)-4-isopropylthiazole

HRID 1422528Notes

Reaction equation

HRID 1422528 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17](O)[C:16]3[C:11](=[C:12]([CH3:22])[C:13]([O:20][CH3:21])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Na+].O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:17]1[C:16]2[C:11](=[C:12]([CH3:22])[C:13]([O:20][CH3:21])=[CH:14][CH:15]=2)[N:10]=[C:9]([C:6]2[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[CH:18]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1784876922-(4-Isopropylthiazol-2-YL)-7-methoxy-8-methylquinolin-4-OL

Product 1

HCID 513586512-(4-Chloro-7-methoxy-8-methylquinolin-2-yl)-4-isopropylthiazoleYield 96%

Procedure

2-(4-Isopropyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-ol (526 mg, 1.67 mmol) was taken up in POCl3 (4.0 mL) and placed in a 85° C. oil bath. The reaction was monitored by LC/MS and determined to be complete after 40 min. The reaction was cooled to rt, and poured into ice water. Adjust pH=10 with 10N NaOH. The mixture was extracted with CH2Cl2, dried with Na2SO4, filtered and was concentrated to afford analytically clean 4-chloro-2-(4-isopropyl-thiazol-2-yl)-7-methoxy-8-methyl-quinoline (532 mg, 96%) as a yellow solid.

Workup

  1. customplaced in a 85° C.
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-bf26c1995f2f467f8b866d34da48998d
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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