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Acetic Acid → 1-(4-chlorobenzyl)-5-((methyl(phenyl)amino)methyl)pyridin-2(1H)-one

HRID 1948203
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1948203
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:25]=[CH:24][C:13]([CH2:14][N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([CH:22]=O)=[CH:16]2)=[CH:12][CH:11]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:9][C:10]1[CH:25]=[CH:24][C:13]([CH2:14][N:15]2[CH:16]=[C:17]([CH2:22][N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:18]=[CH:19][C:20]2=[O:21])=[CH:12][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7515N-MethylanilineHCID 5049666Sodium triacetoxyborohydrideHCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde

Produkt 1

HCID 589669621-(4-chlorobenzyl)-5-((methyl(phenyl)amino)methyl)pyridin-2(1H)-oneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

According to Scheme 7 Method A: A solution of N-methylbenzenamine (1 eq, 0.40 mmol, 0.04 mL) and 1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde (1 eq, 0.40 mmol, 0.10 g) in CH2Cl2 (8 mL) was stirred for 10 min. at room temperature then AcOH (1 eq, 0.40 mmol, 0.02 mL) and NaBH(OAc)3 (1.5 eq, 0.60 mmol, 0.10 g) were added. The reaction mixture was stirred 3 hours at room temperature, was quenched with water and the aqueous phase was extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/MeOH 95/5 followed by crystallization in pentane/diisopropyl ether to afford 1-(4-chlorobenzyl)-5-((methyl(phenyl)amino)methyl)pyridin-2(1H)-one (0.12 mmol, 0.04 g, 29%) as a white solid.

Aufarbeitung

  1. customwas quenched with water
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)
  7. customfollowed by crystallization in pentane/diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-14de7dbf8c81460398c839c022732c82
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399493B2

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