Methanol → HCID 118114022, compound

HRID 706510Notes

Reaction equation

HRID 706510 reaction equation
[I:1][C:2]1[CH:28]=[CH:27][C:5]([NH:6][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[C:11]([O:25][CH3:26])[CH:10]=2)[CH3:8])=[C:4]([N+:29]([O-])=O)[CH:3]=1.[Cl-].[NH4+].CO.O>O1CCCC1.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].[Zn]>[I:1][C:2]1[CH:3]=[C:4]([NH2:29])[C:5]([NH:6][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[C:11]([O:25][CH3:26])[CH:10]=2)[CH3:8])=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 118114016HCID 118114016, compound

Product 1

HCID 118114022HCID 118114022, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62662Ferrous sulfate heptahydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-iodo-N-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethyl)-2-nitroaniline (3.17 g, 5.92 mmol) and ammonium chloride (2.53 g, 47.37 mmol) in tetrahydrofuran (50 mL)/methanol (20 mL)/water (10 mL) was added iron(II) sulfate heptahydrate (5.76 g, 20.73 mmol) and zinc dust (1.35 g, 20.73 mmol). The resulting mixture was heated to reflux. After 1 h, the mixture was allowed to cool to room temperature and was filtered through Celite. The filtercake was washed with methanol (50 mL). The filtrate was concentrated, and the residue was diluted with 3N ammonium hydroxide solution (100 mL). The basic mixture was extracted with chloroform (3×50 mL), and the combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 2.02 g (68%) of 4-iodo-N1-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethyl)benzene-1,2-diamine as a brown solid.

Workup

  1. temperatureThe resulting mixture was heated to reflux
  2. filtrationwas filtered through Celite
  3. washThe filtercake was washed with methanol (50 mL)
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with 3N ammonium hydroxide solution (100 mL)
  6. extractionThe basic mixture was extracted with chloroform (3×50 mL)
  7. dry with materialthe combined organic phases were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bf22b34f370c4061b5c2edc56353808d
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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