Hydrochloric Acid → HCID 20380330, compound

HRID 1448601Notes

Reaction equation

HRID 1448601 reaction equation
C1(C)C=CC=CC=1.Cl[CH2:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:22].[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.Cl>>[CH3:22][C:11]1[CH:12]=[CH:13][CH:14]=[CH:9][C:10]=1[CH:15]([NH:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 17274-AminopyridineHCID 70611067HCID 70611067, compound

Product 1

HCID 20380330HCID 20380330, compoundYield 31%

Procedure

250 Milliliters of toluene containing 10.8 grams (0.05 mole) of chloro(phenyl-o-tolyl)methane and 14.1 grams (0.15 mole) of 4-aminopyridine were heated under reflux with stirring for 20 hours. The reaction mixture was cooled and the resulting organic layer and solid material were stirred with 2 N hydrochloric acid. The toluene layer was removed and the gummy acidic extracts were basified with 5 N sodium hydroxide. The resulting oil was extracted into toluene and washed with water. After drying over magnesium sulphate, the solvent was removed and the residue was recrystallised from toluene to afford 3.58 grams (31% yield) of the title compound, m.p. 141°-143° C. The product may be recrystallised from a mixture of benzene and light petroleum (b.p. 100°-120° C.).

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was cooled
  3. customThe toluene layer was removed
  4. extractionThe resulting oil was extracted into toluene
  5. washwashed with water
  6. dry with materialAfter drying over magnesium sulphate
  7. customthe solvent was removed
  8. customthe residue was recrystallised from toluene

Sources & evidence

ORD record
ord-2720c7e8e859467ea29cc50daddcd479
Source dataset
uspto-grants-1979_12
Patent number
US04180670

Reaction notes

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