Tetrahydrofuran → 6-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile

HRID 81065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81065
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[N:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[CH:3]=1.[Cl-].[NH4+].C1COCC1>[Zn].CO>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([C:8]#[N:9])=[C:6]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:12][CH:11]=3)[N:5]=2)=[CH:28][CH:27]=1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 669270004-Chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile

Produkt 1

HCID 669269446-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrileAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile (136.3 mg, 0.319 mmol), zinc dust (312 mg, 4.78 mmol), ammonium chloride (256 mg, 4.78 mmol), THF (3 mL) and methanol (3 mL) was stirred at room temperature for 15 min, and filtered. The filtrate was concentrated and partitioned with dichloromethane and saturated sodium bicarbonate. The organic layer was separated and concentrated. Silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, gave pure 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile as yellow solid (51 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.96-8.04 (4H, m), 7.70 (1H, s), 7.40 (2H, t, J=8.03 Hz), 7.18 (1H, t, J=7.40 Hz), 7.08-7.14 (4H, m), 6.76 (2H, δ, J=8.78 Hz), 4.04 (2H, s); MS (ES+) m/z: 398 (M+H); LC retention time: 4.551 min (analytical HPLC Method A). Additional impure product was also obtained from the chromatography (48.1 mg).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompartitioned with dichloromethane and saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 0-40% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-509b039825f144e680a55a26c46d6e35
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846673B2

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