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

HRID 1462913Notes

Reaction equation

HRID 1462913 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].[C:15]([S:23][CH:24]([CH3:28])[C:25](Cl)=[O:26])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[C:15]([S:23][CH:24]([CH3:28])[C:25]([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:26])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 129155212-Benzoylthiopropanoyl chlorideHCID 457901311,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochloride

Product 1

HCID 133367612-Quinolinecarboxylic acid,1-[2-(benzoylthio)-1-oxopropyl]-1,2,3,4-tetrahydro-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(±)-1,2,3,4-Tetrahydro-2-quinolinecarboxylic acid hydrochloride (43 g) in pyridine (300 ml) was treated dropwise with 2-benzoylthiopropanoyl chloride (46 g) with vigorous stirring. After stirring at room temperature overnight, the mixture was poured onto ice (300 g) and acidified with concentrated hydrochloric acid. The product was extracted with ether and the ether extracts combined, dried over sodium sulfate, and concentrated to dryness in vacuo. The residue, (±)-1-(2-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was crystallized from acetonitrile (100 ml); yield 7 g, m.p. 157°-159°.

Workup

  1. additionthe mixture was poured onto ice (300 g)
  2. extractionThe product was extracted with ether
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness in vacuo
  5. customThe residue, (±)-1-(2-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was crystallized from acetonitrile (100 ml)

Sources & evidence

ORD record
ord-097e0b73eb7b4cb0b27246120ddf09ef
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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