Hydrochloric Acid → HCID 14281278, compound

HRID 231543Notes

Reaction equation

HRID 231543 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[ClH:19].[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[ClH:19].[C:20]([O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 142812598-(4-Hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline

Product 1

HCID 14281278HCID 14281278, compoundYield 49%

Procedure

A mixture of 4.0 g (15.6 mmol) of 8-(4-hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline in 40 ml of acetic anhydride was heated under reflux for 2 hours. A reagent was then removed under reduced pressure and the residue was subjected to flash chromatography (Kieselgel 60; 5% ethyl acetate in dichloromethane). The thick yellow oil thus obtained was treated with ethereal hydrogen chloride to yield 3.4 g (49%) of 8-(4-acetoxyphenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customA reagent was then removed under reduced pressure
  4. customThe thick yellow oil thus obtained

Sources & evidence

ORD record
ord-87eb8aacaea04a3081b9c8890df08c22
Source dataset
uspto-grants-1989_07
Patent number
US04847268

Reaction notes

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