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

HRID 885456노트

반응식

HRID 885456 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-ab5a8d49632d482e84ee5df6271f7e9d
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242157B2

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