4,4'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(5-(2-methoxyethoxy)-2-nitrobenzonitrile) → 4,4'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(2-amino-5-(2-methoxyethoxy)benzonitrile)

To a solution of 4,4′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(5-(2-methoxyethoxy)-2-nitrobenzonitrile) (0.3 g) in AcOH (10 mL) and i-PrOH (10 mL) was added iron powder (0.75 g). The resulting mixture was heated to reflux for 1 h. After reaction finished, the mixture was cooled to room temperature, filtered, the precipitate washed with EA (10 mL). The combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography to give 0.22 g of 4,4′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(2-amino-5-(2-methoxyethoxy)benzonitrile). 1H-NMR (400 MHz, CDCl3): δ: 6.88 (s, 2H), 6.33 (s, 2H), 4.28 (br, 4H), 4.15-4.12 (m, 4H), 4.05-4.02 (m, 4H), 3.86-3.83 (m, 4H), 3.72-3.68 (m, 8H), 3.66-3.64 (m, 4H), 3.42 (s, 6H).

1. temperatureThe resulting mixture was heated
2. temperatureto reflux for 1 h
3. customAfter reaction
4. filtrationfiltered
5. washthe precipitate washed with EA (10 mL)
6. concentrationThe combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography

ORDレコード

ord-d1272a8fdcf14ea09df3af6e0c1da569

出典データセット

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08916572B2