Hydrochloric Acid → 2-Quinolinecarboxylic acid,1-[(benzoylthio)acetyl]-1,2,3,4-tetrahydro-

HRID 1680522Notes

Reaction equation

HRID 1680522 reaction equation
Cl.[NH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[C:12]([OH:14])=[O:13].Cl[CH2:16][C:17](Cl)=[O:18].[C:20]([O-:28])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[K+].Cl>[OH-].[Na+].O>[C:20]([S:27][CH2:16][C:17]([N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[C:12]([OH:14])=[O:13])=[O:18])(=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 23681850Potassium thiobenzoateHCID 457901311,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochloride

Product 1

HCID 155747312-Quinolinecarboxylic acid,1-[(benzoylthio)acetyl]-1,2,3,4-tetrahydro-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 14798Sodium HydroxideSolvent2×

Procedure

(±)-1,2,3,4-Tetrahydro-2-quinolinecarboxylic acid hydrochloride (26 g) was dissolved in a cold solution of sodium hydroxide (9.6 g) and water (125 ml). The solution was cooled with an ice bath and under vigorous stirring, a solution of sodium hydroxide (4.8 g) and water (60 ml), and chloroacetyl chloride (9.9 ml) were added dropwise. The mixture was stirred for 3 hours at room temperature and then potassium thiobenzoate (21 g) in water (120 ml) was added. This mixture was stirred at room temperature for 18 hours, cooled in an ice bath to 0°, and then acidified with concentrated hydrochloric acid. The product was extracted with chloroform and the extract dried over magnesium sulfate and concentrated to yield (±)-1-(2-benzoylthio-1-oxoethyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid; yield 20 g, m.p. 164°-168°.

Workup

  1. temperatureThe solution was cooled with an ice bath and under vigorous stirring
  2. stirringThis mixture was stirred at room temperature for 18 hours
  3. temperaturecooled in an ice bath to 0°
  4. extractionThe product was extracted with chloroform
  5. dry with materialthe extract dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d05231dd5fa34aecb647a4cf9bc2d259
Source dataset
uspto-grants-1981_06
Patent number
US04273927

Reaction notes

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