Hantzsch ester → HCID 178517028, compound

HRID 1507301Notes

Reaction equation

HRID 1507301 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].BrC1C=C2C(=CC=1)NC(=O)C(C1C=CC=CC=1Cl)=C2O.[F:34][C:35]([F:45])([F:44])[C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][N:37]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>N1C=CC=CC=1.C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[C:6]([CH2:40][C:39]1[CH:38]=[N:37][C:36]([C:35]([F:45])([F:34])[F:44])=[CH:43][CH:42]=1)=[C:5]2[OH:13]

Participants

7

Reactant 4

HCID 70849Hantzsch esterHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 546894466-Bromo-4-hydroxyquinolin-2(1H)-oneHCID 867160586-Bromo-3-(2-chlorophenyl)-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 178517028HCID 178517028, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3776IsopropanolSolvent

Procedure

6-Bromo-4-hydroxyquinolin-2(1H)-one (3.2 g, 18.3 mmol, Intermediate 8: step a), 6-(trifluoromethyl)nicotinaldehyde (4.0 g, 16.7 mmol), and diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (4.2 g, 16.7 mmol), in pyridine (34 mL) were heated to 105° C. for 3 hours. The solution was allowed to cool to ambient temperature, resulting in the formation of a solid. Minimal isopropanol was added to the mixture and the slurry was stirred for 1 hour, sonicated, and filtered. The filtered solids were rinsed with isopropanol and dried under continuous air flow to provide the title compound as an off-white solid. Additional product was recrystallized from the filtrate, filtered, and rinsed with isopropanol.

Workup

  1. customresulting in the formation of a solid
  2. customsonicated
  3. filtrationfiltered
  4. washThe filtered solids were rinsed with isopropanol
  5. customdried under continuous air flow

Sources & evidence

ORD record
ord-663d9c2e41df4be7afd1866e5c47fec6
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

Loading…