Ethyl isonicotinate → HCID 15093859, compound

HRID 1709869Notes

Reaction equation

HRID 1709869 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[CH:17][C:18]=1[F:19].[Cl-].[NH4+]>O1CCCC1>[F:12][C:13]1[CH:14]=[C:15]([C:1]([C:16]2[CH:15]=[CH:14][C:13]([F:12])=[C:18]([F:19])[CH:17]=2)([C:2]2[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=2)[OH:9])[CH:16]=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 3

HCID 15291Ethyl isonicotinateHCID 25517Ammonium ChlorideHCID 178505835HCID 178505835, compound

Product 1

HCID 15093859HCID 15093859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically stirred solution of ethyl isonicotinate in dry tetrahydrofuran at 0° C. and under an atmosphere of nitrogen is slowly added a solution 2.2 equivalents of 3,4-difluorophenyl magnesium bromide in tetrahydrofuran. The solution is stirred at ambient temperature of 4 hr and is poured into an icy solution of ammonium chloride. The mixture is extracted with methylene chloride, and the organic phase is dried (sodium sulfate). The solvent is removed in vacuo to give a solid. This solid is recrystallized from methylene chloride/hexane to give the title compound as a white, crystalline solid, mp 147°-149° C.

Workup

  1. extractionThe mixture is extracted with methylene chloride
  2. dry with materialthe organic phase is dried (sodium sulfate)
  3. customThe solvent is removed in vacuo
  4. customto give a solid
  5. customThis solid is recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-8fa0ae266f3647cc90940e964ec678e2
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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