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Carbon Tetrachloride → 3-Bromomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

HRID 1887822
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887822
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[N:8]=2)=[O:4].C1C(=O)N([Br:34])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH2:15][Br:34])=[CH:11][CH:10]=[C:9]([C:17]([F:18])([F:19])[F:20])[N:8]=2)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 712084863-Methyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

Produkt 1

HCID 866757683-Bromomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester
Ausbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 50 mL pear-shaped flask, 3-methyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (0.45 g, 1.24 mmol), NBS (221 mg, 1.24 mmol) and benzoyl peroxide (60.2 mg, 0.248 mmol) were combined with carbon tetrachloride (12 mL) to give a light yellow suspension. The reaction mixture was refluxed for 2 hr. The reaction mixture was cooled, diluted with methylene chloride (50 mL), washed with saturated aqueous NaHCO3 (1×20 mL), and brine (1×20 mL). The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give crude 3-bromomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (536.6 mg, 97.9%) as a pale yellow solid. The material was not further purified. 1H NMR (DMSO-d6) δ ppm 8.89 (d, J=8.2 Hz, 1H) 7.99 (d, J=8.2 Hz, 1H) 7.44-7.62 (m, 5H) 4.53 (s, 2H) 3.55 (s, 3H). MS calcd. for C18H12BrF3N2O3 [(M+H)+] 442.0, obsd. 443.0.

Aufarbeitung

  1. customto give a light yellow suspension
  2. temperatureThe reaction mixture was refluxed for 2 hr
  3. temperatureThe reaction mixture was cooled
  4. washwashed with saturated aqueous NaHCO3 (1×20 mL), and brine (1×20 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b092afb0670e4f9ab888d4cab73d9680
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501732B2

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