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

HRID 1462904Notes

Reaction equation

HRID 1462904 reaction equation
C(CCC(O)=S)(=O)C.S(Cl)(Cl)=O.[C:13]([S:16][CH2:17][CH2:18][C:19](Cl)=[O:20])(=[O:15])[CH3:14].Cl.[NH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH:24]1[C:33]([OH:35])=[O:34].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:13]([S:16][CH2:17][CH2:18][C:19]([N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH:24]1[C:33]([OH:35])=[O:34])=[O:20])(=[O:15])[CH3:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 129431223-(Acetylsulfanyl)propanoyl chloride2×HCID 457901311,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochlorideHCID 178467872HCID 178467872, compound

Product 1

HCID 133367472-Quinolinecarboxylic acid,1-[3-(acetylthio)-1-oxopropyl]-1,2,3,4-tetrahydro-

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

3-Acetylthiopropanoic acid (132 g) in toluene (200 ml) was treated with thionyl chloride (300 ml). The resulting solution was warmed on the steam bath for two hours, stirred overnight at room temperature then evaporated to dryness under reduced pressure, and finally distilled, to yield 139 g, b.p. (0.35-0.50 mm) 64°-66° of 3-acetylthiopropanoyl chloride. A solution of (±)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid hydrochloride (32.05 g) in pyridine (300 ml) was treated dropwise with 3-acetylthiopropanoyl chloride (25 g) with vigorous stirring. After stirring overnight, the reaction mixture was added to ice (600 g), acidified with concentrated hydrochloric acid, and extracted with ether. The combined ether extracts were concentrated under vacuum to a solid product, which was washed with cold ether (50 ml). This product, 1-(3-acetylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was crystallized from ethyl acetate-hexanes; yield 19 g, m.p. 89°-91°.

Workup

  1. temperatureThe resulting solution was warmed on the steam bath for two hours
  2. customthen evaporated to dryness under reduced pressure
  3. distillationfinally distilled
  4. customto yield 139 g, b.p
  5. stirringAfter stirring overnight
  6. extractionextracted with ether
  7. concentrationThe combined ether extracts were concentrated under vacuum to a solid product, which
  8. washwas washed with cold ether (50 ml)
  9. customThis product, 1-(3-acetylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was crystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-d19230d7b86e42629479acdacba2032e
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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