Hydrochloric Acid → HCID 66596834, compound

HRID 1811382Notes

Reaction equation

HRID 1811382 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8][C:7]=2[C:6]([CH:15]=O)=[CH:5][CH:4]=1.[C:17]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].N1CCCCC1.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:15]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]([O:25][CH2:26][CH3:27])=[O:24])=[C:7]2[C:12]=1[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 86613909HCID 86613909, compound

Product 1

HCID 66596834HCID 66596834, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

8-Methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-5-carboxaldehyde (18.9 g), diethyl malonate (26.5 ml) and piperidine (2.7 ml) were added to pyridine (90 ml), and the resulting mixture was stirred at 90 to 100° C. for 6 hours. After cooling to room temperature, the reaction mixture was added to cold concentrated hydrochloric acid, and the precipitated solid was collected by filtration, washed with water and dried to thereby obtain 16.62 g (yield: 53%) of diethyl 2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethylene)malonate as a yellow powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c0054ba44f2143569eb3f384939cfa93
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

Loading…