Ammonium Chloride → HCID 20291231, compound

HRID 1413952Notes

Reaction equation

HRID 1413952 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[C:10]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>CCOCC>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[OH:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 267314-BenzoylpyridineHCID 178418370HCID 178418370, compound

Product 1

HCID 20291231HCID 20291231, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.05 mole of 4-methylphenyl magnesium bromide in 500 ml of anhydrous ether was treated with 4-benzoylpyridine in 500 ml anhydrous ether. After stirring the resulting mixture for 1.5 hours at 25° , an aqueous solution of ammonium chloride was added causing a solid to form which was filtered. Recrystallization of this material from 95% ethanol afforded the desired α-(4-methylphenyl)-α-phenyl-4-pyridine methanol, m.p. 192°-195° C. The corresponding 4-chlorophenyl (m.p. 198°-202° C.) and 4-methoxyphenyl (m.p. 204°-206° C.) derivatives were also prepared by the same method, using equivalent amounts of the appropriate starting materials.

Workup

  1. customto form which
  2. filtrationwas filtered
  3. customRecrystallization of this material from 95% ethanol

Sources & evidence

ORD record
ord-676db149b86e4a49a76e2d9e41a956f1
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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