Hydrochloric Acid → 8-(4-n-Butoxyphenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 231542Notes

Reaction equation

HRID 231542 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[ClH:21]>CN(C)C=O.CCOCC>[ClH:21].[CH2:9]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 142812598-(4-Hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline

Product 1

HCID 142812748-(4-n-Butoxyphenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

0.72 g (24 mmol) of sodium hydride were added to a solution of 5.15 g (20 mmol) of 8-(4-hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline in 26 ml of dimethylformamide under nitrogen. When effervescence had ceased, 3.29 g (24 mmol) of n-bromobutane were added dropwise with ice-cooling. After stirring at room temperature overnight, the mixture was poured into ice-cold water and extracted with ether to obtain a brown oil. A solution of the oil in ether was treated with ethereal hydrogen chloride to precipitate 4.89 g (70%) of 8-(4-n-butoxyphhenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride as pale yellow crystals (from ethanol-ether).

Workup

  1. temperaturecooling
  2. additionthe mixture was poured into ice-cold water
  3. extractionextracted with ether
  4. customto obtain a brown oil
  5. customto precipitate 4.89 g (70%) of 8-(4-n-butoxyphhenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride as pale yellow crystals (from ethanol-ether)

Sources & evidence

ORD record
ord-d54716f5f8d34fa9952b2a73a841fcb1
Source dataset
uspto-grants-1989_07
Patent number
US04847268

Reaction notes

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