Hydrochloric Acid → 3-(3-Methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehyde

HRID 2053432

Reaction equation

HRID 2053432 reaction equation
C(O[C:4]([C:6]1[C:7](=[O:23])[NH:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12](Cl)=[CH:11][CH:10]=2)=[O:5])C.Cl.[O:25]1[CH2:30]COCC1>O>[CH3:14][C:9]1[CH:10]=[C:4]([C:6]2[C:7](=[O:23])[NH:8][C:9]3[C:14]([C:15]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][C:12]([CH:30]=[O:25])=[CH:11][CH:10]=3)[O:5][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 738703Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylate

Product 1

HCID 1360186723-(3-Methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (200 mg, 0.61 mmol), 10% HCl (1 mL) and dioxane (3 mL) was heated to reflux for 48 h. After cooling, water was added and the resulting precipitate was collected by filtration, washed with water and dried to afford 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid (a) (143 mg, 78%). MS: 300.5 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-dfcf3c603a164719bea5234769eb7fd5
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Linked notes

Loading…