Quinoline → HCID 178425913, compound

HRID 2309827Notes

Reaction equation

HRID 2309827 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.C1([SH:18])C=CC=CC=1.N1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)C=CC=1>>[CH3:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[S:18])=[CH:3][C:2]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 7047QuinolineHCID 7969ThiophenolHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 178425913HCID 178425913, compoundYield 95%

Conditions

Temperature
110 °C

Procedure

A 22 liter 3-necked round bottom flask, fitted with an overhead stirrer, thermometer, and a distillation head was placed in a heating mantle and charged with quinoline (6 liter), 3-bromo-4-methylbenzoic acid (2.75 kg, 12.79 mole), thiophenol (1.75 kg 15.22 mole) and cuprous oxide (958 g, 6.7 mole). The red slurry was placed under a nitrogen blanket and heated with stirring to 180°-200° C. over a 1 hour period collecting the water as it distills. This temperature was maintained for 0.5 hours. The mixture was cooled to 110° C. and then transferred to a stirred solution of 6N hydrochloric acid. After stirring overnight, the product was collected by suction filtration, washed with 6N hydrochloric acid (19 liters) and then with water until neutral (alk-acid paper). The filter cake was washed with isopropanol and dried at 40° C. in vacuo to yield the title compound as a tan solid (2.97 kg, 95% yield, 91% purity).

Workup

  1. customA 22 liter 3-necked round bottom flask, fitted with an overhead stirrer
  2. temperatureheated
  3. customcollecting the water as it
  4. distillationdistills
  5. temperatureThis temperature was maintained for 0.5 hours
  6. stirringAfter stirring overnight
  7. filtrationthe product was collected by suction filtration
  8. washwashed with 6N hydrochloric acid (19 liters)
  9. washThe filter cake was washed with isopropanol
  10. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-bfe4b2b0f0804b17aaaacb72387717f7
Source dataset
uspto-grants-1987_09
Patent number
US04697037

Reaction notes

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