Water → N-Methyl-o-phenylenediamine

HRID 54320

反応式

HRID 54320 の反応式
[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]

参加物

8

反応物 4

HCID 962WaterHCID 69157Benzenamine, N-methyl-2-nitro-HCID 1645844-Fluorobenzene-1,2-diamine2 回HCID 5284359Calcium Chloride

生成物 1

HCID 78498N-Methyl-o-phenylenediamine

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 702Ethanol溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-929d94df6f224bab9b8489fe3fdd290f
出典データセット
uspto-grants-1997_04
特許番号
US05622952

関連ノート

読み込み中…