Sodium Carbonate → Benzenamine, 2,6-dimethoxy-

HRID 1038935

反応式

HRID 1038935 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c1bcec074b514d8eb273703e30ac0b26
出典データセット
uspto-grants-2013_10
特許番号
US08552009B2

関連ノート

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