Sodium Bicarbonate → 2,4,5-Trimethoxyaniline

HRID 601013

반응식

HRID 601013 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[O:14][CH3:15].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([O:14][CH3:15])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[NH2:9]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 8224151,2,4-Trimethoxy-5-nitrobenzeneHCID 85782573Tin tetrachloride dihydrate

생성물 1

HCID 124101382,4,5-Trimethoxyaniline수율 54.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

1,2,4-Trimethoxy-5-nitro-benzene (1.20 g, 5.63 mmol) and tin chloride dihydrate (3.81 g, 16.9 mmol) in ethyl acetate (50 mL) was stirred at 65-70° C. for 20 h. The reaction was cooled, carefully neutralized with sodium bicarbonate and was filtered through Celite. The organic phase was washed with brine, dried (sodium sulfate) and was evaporated. Purification by flash chromatography (SiO2) eluted with 3:7 ethyl acetate:hexanes provided 2,4,5-trimethoxy-phenylamine (0.56 g, 54% yield) as a tan solid. 1H-NMR (DMSO-d6, 500 MHz) 6.57 (s, 1H), 6.37 (s, 1H), 3.70 (s, 3H), 3.65 (s, 3H), 3.63 (s, 3H) ppm; HPLC (Method A) 2.163 min.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationwas filtered through Celite
  3. washThe organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customwas evaporated
  6. customPurification by flash chromatography (SiO2)
  7. washeluted with 3:7 ethyl acetate

출처 및 근거

ORD 기록
ord-a6b536d91ec94f6fbd89326ad637e0d7
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902239B2

연결된 노트

불러오는 중…