Sodium Hydroxide → 2-Amino-5-methylbenzonitrile

HRID 44349

Reaktionsgleichung

Reaktionsgleichung von HRID 44349
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[Sn]Cl.[OH-].[Na+]>Cl.CCO>[NH2:10][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:9][C:6]=1[C:7]#[N:8]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 5607435-Methyl-2-nitrobenzonitrile

Produkt 1

HCID 2427782-Amino-5-methylbenzonitrileAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl2 (11.22 g, 59.2 mmol) in conc. HCl (12 mL) and EtOH (12 mL). The reaction temperature was maintained at 20-30° C. using an ice bath. The reaction mixture was then stirred at room temperature for 1 h and poured into an ice cold aqueous solution of NaOH (6N, app. 30 mL) to neutralize to pH7. The product was extracted into EtOAc, washed with brine, dried over MgSO4 and concentrated to provide the title product (1.56 g, 99%) as a yellow-brown solid. 1H NMR (400 MHz, DMSO-d6) δ2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H). 13C NMR (DMSO-d6) δ20.13, 93.99, 116.12, 118.94, 125.38, 132.32, 135.76, 150.21. MS 133 (MH+).

Aufarbeitung

  1. extractionThe product was extracted into EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1244153bb4e24774985ee81c760e8c2f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541421B2

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