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

HRID 1405965Notes

Reaction equation

HRID 1405965 reaction equation
[O:1]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:31]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:32][C:33]([N+:38]([O-])=O)=[C:34]([CH:37]=1)[C:35]#[N:36])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][C:11]([N+:16]([O-])=O)=[C:12]([CH:15]=1)[C:13]#[N:14]>CC(O)=O.CC(O)C.[Fe]>[O:1]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][C:11]([NH2:16])=[C:12]([CH:15]=1)[C:13]#[N:14])[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:31]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:32][C:33]([NH2:38])=[C:34]([CH:37]=1)[C:35]#[N:36]

Participants

5

Reactant 1

HCID 867011935,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile)

Product 1

HCID 867011925,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile)Yield 82.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile) (0.2 g) in AcOH (10 mL) and i-PrOH (10 mL) was added iron powder (0.5 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 0.15 g of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile). 1H-NMR (400 MHz, CDCl3): δ: 6.90 (s, 2H), 6.25 (s, 2H), 4.20-4.16 (br, 4H), 4.15-4.02 (m, 8H), 3.82-3.79 (m, 4H), 3.77-3.75 (m, 4H), 3.72-3.70 (m, 4H), 3.68-3.66 (m, 4H), 3.43 (s, 6H).

Workup

  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

Sources & evidence

ORD record
ord-d9f497a922f644fe855f1670e2c953a4
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

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