Water → N-Methyl-o-phenylenediamine

HRID 54320

반응식

HRID 54320 반응식
[Cl-].[Cl-].[Ca+2].O.FC1C=CC(N)=C(N)C=1.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O>CCO.CCOCC.[Zn]>[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22]

참가 물질

8

반응물 4

HCID 962WaterHCID 69157Benzenamine, N-methyl-2-nitro-HCID 1645844-Fluorobenzene-1,2-diamine2회HCID 5284359Calcium Chloride

생성물 1

HCID 78498N-Methyl-o-phenylenediamine

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 702Ethanol용매2회HCID 3283Diethyl Ether용매

실험 절차

N-Methyl-1,2-diaminobenzene was prepared using an adaptation of the method of Tsuji et al. (J. Org. Chem. 55:580 (1990)). Zn powder (8.07 g, 0.123 mol), CaCl2 (807 mg), H2O (9.9 mL) and 30 mL EtOH were combined and brought to reflux as described for 4-fluoro-1,2-diaminobenzene (see Example 10), and to this mixture was added slowly dropwise a solution of N-methyl-2-nitroaniline (1.50 g, 9.86 mmol) in 15 mL EtOH. Analysis and workup were as described for 4-fluoro-1,2-diaminobenzene except that the reaction residue was dissolved in 50 ml Et2O. This Et2O solution was then extracted with 3×25 mL 1N HCl and the aqueous layers combined and basified with 5 g of 50% NaOH solution. This solution was then extracted with 3×25 mL Et2O. These Et2O layers were then combined, dried (MgSO4) and the solvent evaporated at reduced pressure to yield 911.1 mg (76.1%) of a dark brown oil. 1H NMR (CDCl2) δ2.87 (s, 3H, CH3), 3.31 (br s, 3H, NH), 6.67 (m, 3H, ArH), 6.86 (m, 1H, ArH).

후처리

  1. temperatureto reflux
  2. extractionThis Et2O solution was then extracted with 3×25 mL 1N HCl
  3. extractionThis solution was then extracted with 3×25 mL Et2O
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated at reduced pressure

출처 및 근거

ORD 기록
ord-929d94df6f224bab9b8489fe3fdd290f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622952

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