Toluene → 4-tert-Butyl-N-(2-chloro-quinolin-3-yl)-benzamide

HRID 1944518

Reaktionsgleichung

Reaktionsgleichung von HRID 1944518
C[Al](C)C.C1(C)C=CC=CC=1.[Cl:12][C:13]1[C:22]([NH2:23])=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[C:24]([C:28]1[CH:37]=[CH:36][C:31]([C:32](OC)=[O:33])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>ClCCCl.CO>[C:24]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([NH:23][C:22]2[C:13]([Cl:12])=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:33])=[CH:36][CH:37]=1)([CH3:27])([CH3:25])[CH3:26]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 97433Methyl p-tert-butylbenzoateHCID 16682925TrimethylaluminumHCID 199728242-Chloroquinolin-3-amine

Produkt 1

HCID 598599114-tert-Butyl-N-(2-chloro-quinolin-3-yl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of trimethylaluminum in toluene (2.0 M, 0.56 mL, 1.12 mmol) was added to a solution of 2-chloro-quinolin-3-ylamine (0.2 g, 1.12 mmol) and methyl 4-tert-butylbenzoate (0.227 mL, 1.18 mmol) in 1,2-dichloroethane (10 mL). The solution was heated at reflux for 6 hours, cooled to room temperature and treated with methanol (˜1 mL). The product was preabsorbed onto silica gel, and purified by flash chromatography, using 10% ethyl acetate in hexane as the eluant to give the product as a colorless solid, 0.32 g (84%). MS: m/z 339 (MH+). 1H NMR (DMSO-d6): δ 1.34 (s, 9 H), 7.60 (d, 2 H), 7.69 (d of d, 1 H), 7.82 (d of d, 1 H), 7.99 (d, 3 H), 8.09 (d, 1 H), 8.67 (s, 1 H) and 10.31 (s, 1 H).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 6 hours
  3. customThe product was preabsorbed onto silica gel
  4. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-19faf2d3a4b740bfb47cc627b16b4c4e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394828B2

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