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Acetic Acid → (4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine

HRID 1949021
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1949021
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([NH2:13])[CH:3]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([NH:13][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[O:15][CH3:14])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 86582-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 576475264-Bromo-6-chloroquinolin-2-amine

Produkt 1

HCID 68574963(4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

4-Bromo-6-chloro-quinolin-2-ylamine (3.12 g, 12 mmol) was dissolved in 100 mL 1,2-dichloroethane. 2-Methoxybenzaldehyde (1.98 g, 15 mmol) and acetic acid (2.91 g, 48 mmol) were added. The reaction mixture was stirred at 40° C. for 3 h. Sodium triacetoxy borohydride (5.99 g, 25 mmol) was added and stirring was continued at room temperature overnight. The reaction mixture was quenched by addition of 200 mL sat. sodiumbicarbonate solution. The mixture was extracted three times with dichloromethane (200 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). (4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine was obtained as an off-white solid (2.2 g, 48%), MS: m/e=379.1 (M+H+).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe reaction mixture was quenched by addition of 200 mL sat. sodiumbicarbonate solution
  4. extractionThe mixture was extracted three times with dichloromethane (200 mL each)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-47ca78fdd5c34dd3a0858b5eb7b6c360
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399674B2

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