Hydrochloric Acid → 3-Quinolineacrylic acid

HRID 1864678Notes

Reaction equation

HRID 1864678 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>O.N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:14][C:15]([OH:17])=[O:16])[CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 836413-Quinolinecarboxaldehyde

Product 1

HCID 14722903-Quinolineacrylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

80 g of 3-quinoline carboxaldehyde, 85 g of malonic acid and 6.50 g of piperidine were added to 350 ml of pyridine, and stirred at 100° C. for 3 hours. After mixing with 1000 ml of distilled water, concentrated HCl was added thereto until pH of the solution became 4.8, and stirred for 1 hour. The resulting solid was filtrated under a reduced pressure, washed with 1500 ml of distilled water, and dried for 15 to 40 hours to obtain 96 g of the title compound as a white solid (yield 95%).

Workup

  1. additionwas added
  2. stirringstirred for 1 hour
  3. filtrationThe resulting solid was filtrated under a reduced pressure
  4. washwashed with 1500 ml of distilled water
  5. customdried for 15 to 40 hours

Sources & evidence

ORD record
ord-2d9fddce9c1f4cdbb33132c77c64904b
Source dataset
uspto-grants-2009_12
Patent number
US07625926B2

Reaction notes

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