Water → 4-iodo-N1-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)benzene-1,2-diamine

HRID 706419Notes

Reaction equation

HRID 706419 reaction equation
[I:1][C:2]1[CH:27]=[CH:26][C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:10]([O:24][CH3:25])[CH:9]=2)=[C:4]([N+:28]([O-])=O)[CH:3]=1.O.[Cl-].[NH4+]>O1CCCC1.C(O)C.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].[Zn]>[I:1][C:2]1[CH:3]=[C:4]([NH2:28])[C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:10]([O:24][CH3:25])[CH:9]=2)=[CH:26][CH:27]=1

Participants

8

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 118114025HCID 118114025, compound

Product 1

HCID 1181141074-iodo-N1-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)benzene-1,2-diamineYield 97%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 62662Ferrous sulfate heptahydrateCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-iodo-N-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-2-nitroaniline (9.10 g, 17.49 mmol) in tetrahydrofuran (50 mL), ethanol (50 mL), and water (10 mL) was added ammonium chloride (7.48 g, 139.9 mmol) and iron (II) sulfate heptahydrate (14.59 g, 52.47 mmol). The bright orange suspension was treated with zinc (3.43 g, 52.47 mmol). The mixture was gradually warmed to reflux. After 3.5 h, the color of the reaction mixture had turned from orange to olive-green. At this point the recation mixture was allowed to cool to room temperature. The mixture was filtered through Celite, and the filtercake was washed with methanol. The filtrate concentrated, the residue was suspended in water. The aqueous mixture was extracted with chloroform (×3). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to afford 8.32 g (97%) of 4-iodo-N1-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)benzene-1,2-diamine as a tan solid.

Workup

  1. temperatureThe mixture was gradually warmed to reflux
  2. filtrationThe mixture was filtered through Celite
  3. washthe filtercake was washed with methanol
  4. concentrationThe filtrate concentrated
  5. extractionThe aqueous mixture was extracted with chloroform (×3)
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f35e30600d1b421db3a9dde1dc670f08
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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