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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)

HRID 1405960
Notes
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Reaction equation

HRID 1405960 reaction equation
[O:1]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:37]([O:38][CH2:39][CH2:40][O:41][CH3:42])=[CH:36][C:33]([C:34]#[N:35])=[C:32]([N+:43]([O-])=O)[CH:31]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([N+:21]([O-])=O)[CH:9]=1>CC(O)=O.CC(O)C.[Fe]>[O:1]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:37]([O:38][CH2:39][CH2:40][O:41][CH3:42])=[CH:36][C:33]([C:34]#[N:35])=[C:32]([NH2:43])[CH:31]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([NH2:21])[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 867011904,4'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(5-(2-methoxyethoxy)-2-nitrobenzonitrile)

Product 1

HCID 867011914,4'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(2-amino-5-(2-methoxyethoxy)benzonitrile)Yield 81%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent
HCID 3776
Isopropanol
Solvent

Procedure

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).

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-d1272a8fdcf14ea09df3af6e0c1da569
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916572B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes