Quinoline → HCID 20372238, compound

HRID 1284268Notes

Reaction equation

HRID 1284268 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:19])([F:18])[C:9]([F:17])([F:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:20]1C2C(=CC=CC=2)C=C[CH:21]=1>CN(C)C=O>[F:18][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:21]#[N:20])([F:19])[C:9]([F:17])([F:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 20372298HCID 20372298, compound

Product 1

HCID 20372238HCID 20372238, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.33 g. (0.01 mole) of 2-bromo-α,α,α',α'-tetrafluorobibenzyl, 2.70 g. of cuprous cyanide, 30 ml. of dry quinoline, and 3 ml. of dry dimethylformamide are stirred and heated to refluxing for about 30 hours. After cooling and dilution with ether, the precipitate is removed by filtration and washed with ether. Solvents are evaporated from the filtrate under reduced pressure leaving the product as an oily brown solid. Purification is effected by column chromatography on 150 g. of silica, the product being eluted with benzene-hexane (3:1). The fractions which show one spot of rf 0.7 on a silica thin layer plate developed with benzene are combined. Evaporation of the solvents under reduced pressure leaves white crystals, m.p. 84°-86°C. A sample for analysis is sublimed at 55°C. and 0.05 mm; m.p. 85°-86°C.

Workup

  1. additionA mixture of 3.33 g
  2. temperatureheated
  3. temperatureto refluxing for about 30 hours
  4. temperatureAfter cooling
  5. customdilution with ether, the precipitate is removed by filtration
  6. washwashed with ether
  7. customSolvents are evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-057ff9705f9945b8885734a59d512455
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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