Dimethylformamide → 2-Chloro-5-methylpyridine-3-carbaldehyde

HRID 1018021Notes

Reaction equation

HRID 1018021 reaction equation
CN(C)C=[O:4].O=[C:7]([Cl:13])OC(Cl)(Cl)Cl.[CH2:14]([N:21](C=CC)C(=O)C)[C:15]1[CH:20]=C[CH:18]=[CH:17][CH:16]=1>>[Cl:13][C:7]1[C:17]([CH:18]=[O:4])=[CH:16][C:15]([CH3:20])=[CH:14][N:21]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10426DiphosgeneHCID 53742793N-benzyl-N-(1-Propenyl)acetamide

Product 1

HCID 98340182-Chloro-5-methylpyridine-3-carbaldehydeYield 93.4%

Conditions

Temperature
75 °C

Procedure

Dimethylformamide (19.34 g, 0.264 moles) was added to a well stirred and cooled material of diphosgene (36.64 g, 0.185 moles) at 4° C. in 30 minutes in an ice bath followed by N-benzyl-N-(1-Propenyl)acetamide (5 g, 0.026 moles) at the same temperature. The reaction mixture was further continued for 2 hours at 30° C. The ice cold both was removed and heated to 75° C. for 8 hours. Work up procedure was carried out according to the procedure of example 1. Before that excess DMF was removed under reduced pressure. The obtained residue was subjected to chromatographic purification on silica gel to give 2-chloro-5-methylpyridine-3-carbaldehyde (3.78 g) in 92% yield.

Workup

  1. customThe ice cold both was removed
  2. customBefore that excess DMF was removed under reduced pressure
  3. customThe obtained residue was subjected to chromatographic purification on silica gel

Sources & evidence

ORD record
ord-0ba8bf2ce7a84cafb662289fc729be90
Source dataset
uspto-grants-2002_11
Patent number
US06479664B1

Reaction notes

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