Hydrochloric Acid → (+/-) 1-(3-Acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

HRID 1462909Notes

Reaction equation

HRID 1462909 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:18][CH2:19][CH:20]([CH2:24][S:25][C:26](=[O:28])[CH3:27])[C:21](Cl)=[O:22])(=[O:17])[CH3:16].Cl>N1C=CC=CC=1>[C:15]([S:18][CH2:19][CH:20]([CH2:24][S:25][C:26](=[O:28])[CH3:27])[C:21]([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:22])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 129261603-Acetylthio-2-acetylthiomethylpropionyl chlorideHCID 457901311,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochloride

Product 1

HCID 13336756(+/-) 1-(3-Acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (±)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid hydrochloride (14.52 g) in pyridine (150 ml) was treated dropwise with 3-acetylthio-2-(acetylthiomethyl)propanoyl chloride with vigorous stirring. After stirring overnight at room temperature, the mixture was added to ice (300 g) and the pH was adjusted to 2.5 with concentrated hydrochloric acid. The mixture was extracted with ether and the ether extract dried over sodium sulfate and evaporated to a syrup. This (±) 1-(3-acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was further purified by column chromatography (silica gel, toluene:ethyl acetate:acetic acid, 6.5:3:0.5); yield 2.5 g, m.p. 149°-151°.

Workup

  1. extractionThe mixture was extracted with ether
  2. extractionthe ether extract
  3. dry with materialdried over sodium sulfate
  4. customevaporated to a syrup
  5. customThis (±) 1-(3-acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was further purified by column chromatography (silica gel, toluene:ethyl acetate:acetic acid, 6.5:3:0.5)

Sources & evidence

ORD record
ord-ed5e7293cbf049a8ba5ea7dfad9732a7
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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