Methanol → 3-(4-tert-Butyl-phenyl)-N-(2-chloro-quinolin-3-yl)-acrylamide

HRID 1944519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944519
C[Al](C)C.[Cl:5][C:6]1[C:15]([NH2:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.[C:17]([C:21]1[CH:32]=[CH:31][C:24]([CH:25]=[CH:26][C:27](OC)=[O:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].CO>ClCCCl>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([CH:25]=[CH:26][C:27]([NH:16][C:15]2[C:6]([Cl:5])=[N:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:28])=[CH:31][CH:32]=1)([CH3:20])([CH3:18])[CH3:19]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 16682925TrimethylaluminumHCID 199728242-Chloroquinolin-3-amineHCID 53432925Methyl 4-tert-butylcinnamate

Produkt 1

HCID 725804403-(4-tert-Butyl-phenyl)-N-(2-chloro-quinolin-3-yl)-acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of trimethylaluminum (2.0 M, 0.61 mL, 1.22 mmol) was added to a solution of 2-chloro-quinolin-3-ylamine (0.2 g, 1.12 mmol) and methyl 4-tert-butylcinnamate (0.241 g, 1.11 mmol) in 1,2-dichloroethane (10 mL). The solution was heated at reflux for 6 hours. The solution was cooled and treated with methanol (˜1 mL). The product was preabsorbed on silica gel and eluted with 20% ethyl acetate in hexane, to give the product as a colorless solid, 0.288 g (71%). MS: m/z 365 (MH+). 1H NMR (DMSO-d6): δ 1.31 (m, 9 H), 7.16 (d, 1 H), 7.50 (d, 2 H), 7.59-7.69 (m, 4 H), 7.75 (t, 1 H), 7.95 (d, 1 H), 8.05 (d, 1 H), 8.94 (s, 1 H), and 9.97 (s, 1 H).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe solution was cooled
  4. customThe product was preabsorbed on silica gel
  5. washeluted with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-eef5d6d4fda44efda629bd2acc0d1e57
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394828B2

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