Quinoline → HCID 86734815, compound

HRID 436715Notes

Reaction equation

HRID 436715 reaction equation
[Cl:1][CH2:2][C:3]1[C:16]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>C(O)(C)C>[Cl-:1].[C:3]1([CH2:2][N+:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:16]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 11064161HCID 11064161, compound

Product 1

HCID 86734815HCID 86734815, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent4×

Conditions

Temperature
125 °C

Procedure

90 g. of the chloromethylphenanthrene prepared above was placed in a reaction vessel, along with 61.5 g. of crude quinoline. The resulting mixture was then stirred and heated to a temperature of 125° C. A total of 101 g. of isopropanol was weighed out and a portion of this was added to the reaction mixture to permit temperature maintenance of the reaction mixture by refluxing of the isopropanol portion. After the mixture had been held at 125° C. temperature for about 3 hours, the material was cooled to room temperature and the remainder of the isopropanol was added. This resulted in a 60% isopropanol solution of N-(phenanthrylmethyl) quinolinium chloride.

Workup

  1. customwas placed in a reaction vessel, along with 61.5 g
  2. additiona portion of this was added to the reaction mixture
  3. customhad been held at 125° C.
  4. customfor about 3 hours
  5. temperaturethe material was cooled to room temperature

Sources & evidence

ORD record
ord-3e1a98852b9d45ea9f2a0234b05721b2
Source dataset
uspto-grants-1977_06
Patent number
US04028268

Reaction notes

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