Hydrochloric Acid → HCID 70524412, compound

HRID 1995742Notes

Reaction equation

HRID 1995742 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.Cl>N1C=CC=CC=1.CCOCC>[C:11]([N:1]1[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7412Benzoyl chlorideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 70524412HCID 70524412, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 26.6 g (0.02 m) of tetrahydroquinoline in 50 ml of pyridine, cooled to 0° C., there were added 28.1 g (0.02 m) of benzoyl chloride dropwise and with stirring at a rate such the temperature was kept below -5° C. After addition was complete, the mixture was stirred at room temperature for 1 hour and then poured into a separatory funnel containing 500 ml of water and 50 ml of conc. hydrochloric acid. Ethyl ether (300 ml) was added to the funnel and the mixture shaken until all of the precipitated oil had dissolved in the ether. After washing with water, the ether layer was filtered through anhydrous calcium sulfate and evaporated to a volume of about 150 ml. Petroleum ether (100 ml) was added to the solution which was then cooled in a refrigerator to give 35.7 g (75% yield) of 1-benzoyltetrahydroquinoline as colorless crystals, m.p. 80°-81° C.

Workup

  1. customwas kept below -5° C
  2. additionAfter addition
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. additionpoured into a separatory funnel
  5. stirringthe mixture shaken until all of the precipitated oil
  6. washAfter washing with water
  7. filtrationthe ether layer was filtered through anhydrous calcium sulfate
  8. customevaporated to a volume of about 150 ml
  9. additionPetroleum ether (100 ml) was added to the solution which
  10. temperaturewas then cooled in a refrigerator

Sources & evidence

ORD record
ord-73fe79eee3814b50a1ccc7b86f6615bf
Source dataset
uspto-grants-1983_09
Patent number
US04405788

Reaction notes

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