Pyridine → 2-Cyano-3-nitrobenzyl acetate

HRID 471673노트

반응식

HRID 471673 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 674016552-Cyano-3-nitrobenzyl acetate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-99156598eaeb43398a60b91a81b65415
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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