1-(Bromomethyl)-4-chlorobenzene → 1-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde

HRID 1948202Notes

Reaction equation

HRID 1948202 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][N:4]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:4]2[C:3](=[O:2])[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5]2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehydeYield 68%

Procedure

According to Scheme 2: The title compound was prepared from 6-methoxynicotinaldehyde (1 eq, 13.4 mmol, 1.83 g) and 4-chloro-benzylbromide (2 eq, 26.8 mmol, 5.50 g) according to the procedure described for Example 6 Step 2. Reaction conditions: 17 hours under reflux. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 95/5 as eluent to afford 1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde (9.08 mmol, 2.25 g, 68%) as an orange solid.

Workup

  1. customReaction conditions
  2. temperature17 hours under reflux
  3. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-5200252ddf3d415580c4e796e29def23
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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