Ammonium formate → N1,5-Dimethylbenzene-1,2-diamine

HRID 885456ノート

反応式

HRID 885456 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[N+:10]([O-])=O.C([O-])=O.[NH4+]>C1COCC1.CO.[Pd]>[CH3:9][C:7]1[CH:8]=[C:3]([NH:2][CH3:1])[C:4]([NH2:10])=[CH:5][CH:6]=1

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 10103510N,5-Dimethyl-2-nitroaniline

生成物 1

HCID 9989323N1,5-Dimethylbenzene-1,2-diamine

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl-(5-methyl-2-nitro-phenyl)-amine (2.47 g, 14.9 mmol), ammonium formate (15 g, 237.9 mmol) in THF (7 mL) and MeOH (35 mL) at room temperature was added 10% Pd/C (650 mg) and the resuitng mixture was stirred at room temperature for 10 min. The resulting mixture was then filtered over CELITE® and concentrated in vacuo. The resulting residue was diluted with CH2Cl2, washed with H2O and the organic layer dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by flash column chromatography (SiO2), eluting with a hexanes-EtOAc gradient to yield 4,N2-dimethyl-benzene-1,2-diamine

後処理

  1. filtrationThe resulting mixture was then filtered over CELITE®
  2. concentrationconcentrated in vacuo
  3. additionThe resulting residue was diluted with CH2Cl2
  4. washwashed with H2O
  5. dry with materialthe organic layer dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by flash column chromatography (SiO2)
  9. washeluting with a hexanes-EtOAc gradient

出典と根拠

ORDレコード
ord-ab5a8d49632d482e84ee5df6271f7e9d
出典データセット
uspto-grants-2012_08
特許番号
US08242157B2

反応ノート

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