Diisopropylethylamine → N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline

HRID 2178424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2178424
F[C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].Cl.[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=3)=[CH:4][C:3]=2[N+:20]([O-:22])=[O:21])=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27240964-Bromobenzylamine hydrochlorideHCID 904169762-((4-Fluoro-3-nitrophenoxy)methyl)quinoline

Produkt 1

HCID 90414040N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)anilineAusbeute 113,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a 250 mL round-bottomed flask were added a stir bar, 2-((4-fluoro-3-nitrophenoxy)methyl)quinoline (15.0 g, 40 mmol) and 4-bromobenzyl amine hydrochloride (11 g, 50 mmol), DMA (130 mL), and DIPEA (22 mL, 125 mmol). The resulting mixture was heated to 100° C. After 24 h, the mixture was cooled and concentrated to dryness. The residue was triturated with IPA (200 mL) and the orange solid was collected by vacuum filtration. The collected solid was washed with IPA (2×50 mL) and hexanes (2×50 mL) to afford the title compound (21 g, 84%). MS (ESI): mass calcd. for C23H18BrN3O3, 463.05; m/z found 464.1 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.34-8.27 (m, 1H), 8.21 (d, J=8.4, 1H), 8.12-8.06 (m, 1H), 7.87-7.81 (m, 2H), 7.75 (ddd, J=8.4, 6.9, 1.4, 1H), 7.63 (d, J=8.5, 1H), 7.58-7.53 (m, 1H), 7.49-7.46 (m, 2H), 7.25-7.18 (m, 3H), 6.71 (d, J=9.4, 1H), 5.34 (s, 2H), 4.49 (d, J=5.8, 2H).

Aufarbeitung

  1. additionTo a 250 mL round-bottomed flask were added a stir bar
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated to dryness
  4. customThe residue was triturated with IPA (200 mL)
  5. filtrationthe orange solid was collected by vacuum filtration
  6. washThe collected solid was washed with IPA (2×50 mL) and hexanes (2×50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-0a0f55cd9ee34d0abe13cc3aff3b34d6
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067917B2

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