Pyridine → 2-Cyano-3-nitrobenzyl acetate

HRID 711811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711811
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:11]=1[C:12]#[N:13].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:5]([O:4][CH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:11]=1[C:12]#[N:13])(=[O:7])[CH3:6]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 674010342-(Hydroxymethyl)-6-nitrobenzonitrile

Produkt 1

HCID 674016552-Cyano-3-nitrobenzyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetic anhydride (0.84 mL, 8.87 mmol) was added to a solution of 2-(hydroxymethyl)-6-nitrobenzonitrile (Example 207d) (0.31 g, 1.77 mmol), pyridine (0.86 mL, 10.6 mmol), and DMAP (0.22 g, 1.77 mmol) in CH2Cl2 (10 mL), and stirred for 24 h at rt. The mixture was washed once with AcOH (1 M, 20 mL), dried with MgSO4, concentrated, and purified by chromatography on silica using CH2Cl2, to give the title compound in amount of 0.36 g (92%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 5.35 (s, 2H), 7.99 (t, J=8.0 Hz, 1H), 8.06 (dd, J=0.8, 8.0 Hz, 1H), 8.37 (dd, J=0.8, 8.0 Hz, 1H).

Aufarbeitung

  1. washThe mixture was washed once with AcOH (1 M, 20 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. custompurified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-838f71dd0de54ea5b9d12602b90f174c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181276B2

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