Acetic Acid → 1-(4-Nitrophenyl)ethanamine

HRID 1502928

반응식

HRID 1502928 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])=O.[NH4+:16].C(O)(=O)C>[Ir].CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH2:16])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 7487p-NitroacetophenoneHCID 2723923Ammonium formate

생성물 1

HCID 5919951-(4-Nitrophenyl)ethanamine

시약·촉매·용매 2

HCID 23924Iridium촉매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

826 mg (5.0 mmol) of 4′-nitroacetophenone (MW: 165.15), 946 mg (15.0 mmol) of ammonium formate (MW: 63.06) and 5.90 mg (0.01 mmol, S/C=500) of the iridium catalyst Ir-7 (MW: 590.13) were introduced in a 20-mL Schlenk tube, and subjected to argon-gas replacement. To this, 5 mL of dehydrated methanol and 286 μL (5.0 mmol) of acetic acid were added and stirred while heating at 60° C. for 3 hr. After distillation of the solvent, a saturated sodium hydrogen carbonate solution was added, then a product was extracted with methylene chloride, the organic layer was washed with water, and the product was dried with sodium sulfate. The drying agent was removed by filtration and the methylene chloride was distilled away to give a crude product DL-1-(4′-nitrophenyl)ethylamine. Its conversion rate was 100% based on NMR measurement, with 96% of DL-1-(4′-nitrophenyl)ethylamine, 1% of 1-(4′-nitrophenyl)ethanol, and 3% of other by-products. Since no compound in which reduction of nitro groups occurred was generated, we confirmed that reductive amination reaction was carried out in a functional-group-selective manner.

후처리

  1. distillationAfter distillation of the solvent
  2. additiona saturated sodium hydrogen carbonate solution was added
  3. extractiona product was extracted with methylene chloride
  4. washthe organic layer was washed with water
  5. dry with materialthe product was dried with sodium sulfate
  6. customThe drying agent was removed by filtration
  7. distillationthe methylene chloride was distilled away

출처 및 근거

ORD 기록
ord-696e4fe878714a2abe0303fa9cffedc6
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09211533B2

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