Pyridine → 2-Cyano-3-nitrobenzyl acetate

HRID 471673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471673
[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 mice 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 mice 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-99156598eaeb43398a60b91a81b65415
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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