Hydrochloric Acid → HCID 14281280, compound

HRID 231544Notes

Reaction equation

HRID 231544 reaction equation
[N:1]1[C:10]2[CH:9]([S:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[ClH:21].[CH3:22]O>>[ClH:21].[N:1]1[C:10]2[CH:9]([S:11][C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:22])=[O:17])=[CH:19][CH:20]=3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 14281272HCID 14281272, compound

Product 1

HCID 14281280HCID 14281280, compoundYield 62%

Procedure

4.24 g (15 mmol) of 4-(5,6,7,8-tetrahydroquinoline-8-ylthio)-benzoic acid prepared by a method analogous to Example 1 were stirred in 30 ml of refluxing methanol saturated with hydrogen chloride for 2 hours and the solvent was then removed under reduced pressure. The residue was dissolved in iced water, made alkaline with sodium carbonate and extracted with ether. The residue obtained upon evaporation of the solvent was treated with ethereal hydrogen chloride to yield 2.9 g (62%) of methyl 4-(5,6,7,8-tetrahydroquinoline-8-ylthio)-benzoate hydrochloride.

Workup

  1. customthe solvent was then removed under reduced pressure
  2. dissolutionThe residue was dissolved in iced water
  3. extractionextracted with ether
  4. customThe residue obtained upon evaporation of the solvent

Sources & evidence

ORD record
ord-080c9f97acc0481eb496c0739c476444
Source dataset
uspto-grants-1989_07
Patent number
US04847268

Reaction notes

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