Methanol → 2-(Allyloxy)-4-aminobenzonitrile

HRID 474234노트

반응식

HRID 474234 반응식
[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH:2]=[CH2:3].CO.[Cl-].[NH4+]>[Fe].O>[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH:2]=[CH2:3]

참가 물질

6

반응물 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 597543072-(Allyloxy)-4-nitrobenzonitrile

생성물 1

HCID 597542362-(Allyloxy)-4-aminobenzonitrile수율 94%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매2회

반응 조건

온도
65 °C

실험 절차

Iron powder-325 mesh (5.7 g, 98.0 mmol) was taken in a round bottom flask charged with a mixture of 2-(allyloxy)-4-nitrobenzonitrile (4.0 g, 19.6 mmol), absolute methanol (40 mL), water (8 mL) and ammonium chloride (5.2 g, 98 mmol). A water-cooled reflux condenser was attached to the flask and the heterogeneous mixture was heated to 65° C. with vigorous stirring for 50 min. The reaction mixture was filtered, and washed with methanol. The solvent was removed in vacuo. EtOAc was added to the residue, and the solution was washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 2-(allyloxy)-4-aminobenzonitrile (3.2 g, 94% yield) as a light-brown solid. LC-MS (M+H)+=175.2 1H NMR (400 MHz, CDCl3) δ ppm 7.29 (d, 1H, J=8.4 Hz), 6.22 (dd, 1H, J=2.0, 8.4 Hz), 6.14 (s, 1H), 6.07-5.98 (m, 1H), 5.48 (dd, 1H, J=1.6, 3.2 Hz), 5.44 (dd, 1H, J=1.6, 3.2 Hz), 4.59 (d, 2H, J=1.6 Hz).

후처리

  1. temperaturereflux condenser
  2. filtrationThe reaction mixture was filtered
  3. washwashed with methanol
  4. customThe solvent was removed in vacuo
  5. additionEtOAc was added to the residue
  6. washthe solution was washed with water and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-945d4a9acd534b9284b05514d5aa63c8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637523B2

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