Acetic Acid → 1-(4-Nitrophenyl)ethanamine

温度

60 °C

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.

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

ORDレコード

ord-696e4fe878714a2abe0303fa9cffedc6

出典データセット

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09211533B2