Triethylamine → HCID 23503602, compound

HRID 1835424Notes

Reaction equation

HRID 1835424 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[C:23]([CH3:31])[C:11]=1[C:12]([C:14]1[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Cl)[C:15]=1[Cl:22])=[O:13]>[C].[Pd].CO>[CH3:8][O:9][C:10]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[C:23]([CH3:31])[C:11]=1[C:12]([C:14]1[C:19]([Cl:20])=[CH:18][N:17]=[CH:16][C:15]=1[Cl:22])=[O:13]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 235035964-(2,3,4-Trimethoxy-6-methylbenzoyl)-2,3,5-trichloropyridine

Product 1

HCID 23503602HCID 23503602, compoundYield 708%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4.6 g (6.9 mmol) of triethylamine and 1.8 g of 10% palladium carbon were added to a methanol 280 ml solution of 17.8 g (4.6 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,3,5-trichloropyridine (compound No. 186), followed by stirring under hydrogen atmosphere at room temperature for 7 hours. The mixture was subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 11.6 g (yield 72%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3,5-dichloropyridine (compound No. 191; m.p. 109-111° C.).

Workup

  1. filtrationThe mixture was subjected to filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe crude product thus obtained
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7aa35d2a86ef45e7bcff17783229c5e3
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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