Dimethylformamide → 4-Chloropyridine-3-carbaldehyde

HRID 1830857Notes

Reaction equation

HRID 1830857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.CN([CH:31]=[O:32])C>O1CCCC1.CCCCCC>[Cl:1][C:2]1[C:7]([CH:31]=[O:32])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 122884-ChloropyridineHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 140466744-Chloropyridine-3-carbaldehydeYield 86.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution (50 ml) of 4-chloropyridine (25.0 g, 0.22 mol) in tetrahydrofuran was added dropwise to a tetrahydrofuran solution (300 ml) of lithium diisopropylamide prepared from a solution (179 ml, 0.29 mol) of 1.6 M n-butyllithium in hexane and diisopropylamine (33.4 g, 0.33 mol) under an argon atmosphere at −78° C. After stirring for 30 min., DMF (19.3 g, 0.26 mol) was added and the mixture was gradually heated to room temperature. The reaction mixture was extracted with ethyl acetate (200 ml)-5% NH4Cl aq. (300 ml). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give a crude title compound (27 g, 86%) as an oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (200 ml)-5% NH4Cl aq. (300 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8ee7537abe94b829c05c9b0b54dde9c
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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