Sodium Carbonate → Benzenamine, 2,6-dimethoxy-

HRID 1038935

반응식

HRID 1038935 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[N+:11]([O-])=O.C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O.CCO.O.[Fe]>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[NH2:11]

참가 물질

7

반응물 2

HCID 10340Sodium CarbonateHCID 3247841,3-Dimethoxy-2-nitrobenzene

생성물 1

HCID 95940Benzenamine, 2,6-dimethoxy-수율 98%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

To a solution of 78 (170 mg, 0.93 mmol) in AcOH (5 mL), EtOH (5 mL) and H2O (2.5 mL) was added iron powder (311 mg, ˜325 mesh, 5.57 mmol) portion wise. The mixture was then heated at 90° C. under N2 overnight. After cooling to room temperature, the mixture was poured onto ice, basified using solid Na2CO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 79 as a pale yellow solid (139 mg, 98%). MS (APCI): m/z 154 (100%, [M+H]+) which was used in the next step without further purification.

후처리

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto ice
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c1bcec074b514d8eb273703e30ac0b26
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552009B2

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