Pyridine → 2-Cyano-3-nitrobenzyl acetate

HRID 711811ノート

反応式

HRID 711811 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 674016552-Cyano-3-nitrobenzyl acetate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-838f71dd0de54ea5b9d12602b90f174c
出典データセット
uspto-grants-2015_11
特許番号
US09181276B2

反応ノート

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