Aniline → N-phenylquinolin-3-amine

HRID 2175456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175456
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1C=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[C:14]1([NH:13][C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 6115AnilineHCID 796192-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 11117560N-phenylquinolin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of quinoline-3-carbaldehyde 11 (79 mg, 0.5 mmol) in MeOH (5 mL) was added aniline (0.05 mL, 0.55 mmol) and ZnCl2 (136 mg, 2.0 mmol) and the reaction was stirred at room temperature for 15 min. Then NaCNBH3 (62.8 mg, 2.0 mmol) was added and to the reaction was stirred overnight at room temperature. The solvent was removed by rotary evaporation and the residue suspended in EtOAc. The organic layers were combined and washed with NaHCO3, water, and brine and then dried over MgSO. Concentration in vacuo gave the crude product, which was used in the next step without further purification. 1H NMR (CDCl3): 9.05 (s, 1H), 8.23 (d, J=7.6 Hz, 2H), 7.77 (d, J=8.0 Hz, 1H), 7.71-7.66 (m, 1H), 7.54-7.51 (m, 1H), 7.21-7.16 (m, 2H), 6.76-6.72 (m, 1H), 6.68-6.60 (m, 2H), 4.54 (s, 2H), 4.16 (s, br, 1H).

Aufarbeitung

  1. stirringwas stirred overnight at room temperature
  2. customThe solvent was removed by rotary evaporation
  3. washwashed with NaHCO3, water, and brine
  4. dry with materialdried over MgSO
  5. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5174dc4e06d444248492c68de7413b30
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062072B2

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