Dimethylformamide → 2-(4-Methylphenyl)isonicotinaldehyde

HRID 22260Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:3]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].[Cl-].[NH4+]>O1CCCC1>[CH:22]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:3]=1)=[O:23]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 4-bromo-2-(4-methylphenyl)pyridine (3.2 g) in 30 ml of tetrahydrofuran was cooled to -70° C., and 1.6M n-butyl lithium (8.1 ml) was added. The solution was stirred for 15 minutes at -70° C., and then dimethylformamide (1.3 ml) added. The mixture was allowed to warm slowly to room temperature over a period of 2 hours, and aqueous saturated ammonium chloride solution added. The mixture was partitioned between methylene chloride and water, the organic layer separated and dried over sodium sulfate, the solvent evaporated under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 20% ethyl acetate in heptane, to yield 0.81 g of 4-formyl-2-(4-methylphenyl)pyridine, m.p. 66° C.

Workup

temperatureto warm slowly to room temperature over a period of 2 hours
customThe mixture was partitioned between methylene chloride and water
customthe organic layer separated
dry with materialdried over sodium sulfate
customthe solvent evaporated under reduced pressure
customthe residue flash-chromatographed on silica gel
washeluting with 20% ethyl acetate in heptane

Sources & evidence

ORD record: ord-a384d342fec54f5f99058dab40e7de5e
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428037

Reaction notes

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