Benzene → 4-Fluorobenzene-1,2-diamine

HRID 54304

반응식

HRID 54304 반응식
[Cl-].[Cl-].[Ca+2].O.[F:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1.C1C=CC=CC=1>CCO.[Zn].CCOC(C)=O>[F:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([NH2:13])[CH:7]=1

참가 물질

8

반응물 4

HCID 241BenzeneHCID 962WaterHCID 677694-Fluoro-2-nitroanilineHCID 5284359Calcium Chloride

생성물 1

HCID 1645844-Fluorobenzene-1,2-diamine

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 702Ethanol용매2회HCID 8857Ethyl Acetate용매

실험 절차

4-Fluoro-1,2-diaminobenzene was prepared using an adaptation of the method of Tsuji et al. (Tsuji, Y. et al., J. Org. Chem. 55:580 (1990)). A suspension of Zn powder (10.5 g, 0.160 mol), CaCl2 (1.05 g) and H2O in 40 ml EtOH was heated to reflux with stirring under N2. To this was added slowly dropwise a solution of 4-fluoro-2-nitroaniline (2.00 g, 12.8 mmol) in 10 mL EtOH. The reaction mixture was refluxed 8 h. TLC analysis (silica gel, 2:1 benzene:EtOAc) indicated complete disappearance of the starting material. The Zn was removed by vacuum filtration, and the solvent rotary evaporated. The residue was dissolved in 50 mL Et2O and the solution extracted with 3×25 mL 1N HCl. The aqueous layers were combined and basified with 50% aq. NaOH (6 g) and the resulting solution extracted with 3×25 mL Et2O. The Et2O layers were combined and dried (MgSO4). The solvent was rotary evaporated to yield 1.36 g (84%) of a brown solid. mp 90° 92° C. 1H NMR (CDCl3) δ3.18 (brs, 2H, NH2); 3.58 (brs, 2H, NH2); 6.44 (m, 2H, ArH), 6.61 (m, 1H, ArH).

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was refluxed 8 h
  4. customThe Zn was removed by vacuum filtration
  5. dissolutionThe residue was dissolved in 50 mL Et2O
  6. extractionthe solution extracted with 3×25 mL 1N HCl
  7. extractionthe resulting solution extracted with 3×25 mL Et2O
  8. dry with materialdried (MgSO4)
  9. customThe solvent was rotary evaporated

출처 및 근거

ORD 기록
ord-5854a670d5914aab9c66b7ae4530f169
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622952

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