Water → 8-(4-Hydroxy-3-nitrophenylthio)-5,6,7,8-tetrahydroquinoline

HRID 231545

Reaction equation

HRID 231545 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.[N+:19]([O-])([O-:21])=[O:20].[Na+].[N+]([O-])([O-])=O.[La+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.O>CCOCC.Cl>[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][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 24268Sodium NitrateHCID 25122Lanthanum nitrateHCID 14281259HCID 14281259, compound

Product 1

HCID 142812818-(4-Hydroxy-3-nitrophenylthio)-5,6,7,8-tetrahydroquinolineYield 31.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

15.0 g (58 mmol) of 8-(4-hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline in 90 ml of ether were added dropwise to a stirred solution of 4.96 g (58 mmol) of sodium nitrate and 0.25 g (58 mmol) of lanthanum nitrate in 60 ml of 5.5N hydrochloric acid at 0° to 5° C. in an ice-bath. Stirring was then continued under nitrogen for 24 hours, after which water was added and the mixture was extracted with chloroform. Removal of solvent left a yellow oil which was purified by flash chromatography (Kieselgel 60; 10% ethyl acetate in dichloromethane) to obtain 5.6 g (20%) of 8-(4-hydroxy-3-nitrophenylthio)-5,6,7,8-tetrahydroquinoline as yellow crystals (from ethanol).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customRemoval of solvent
  3. waitleft a yellow oil which
  4. customwas purified by flash chromatography (Kieselgel 60; 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-72b5ba91b0d649788b969ca8cf92641f
Source dataset
uspto-grants-1989_07
Patent number
US04847268

Linked notes

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