Water → N1-(2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-4-iodobenzene-1,2-diamine

HRID 706465Notes

Reaction equation

HRID 706465 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C:17]([O:30][CH3:31])=[CH:16][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[N+:13]([O-])=O.O.[Cl-].[NH4+]>O1CCCC1.CO.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].[Zn]>[F:1][C:2]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C:17]([O:30][CH3:31])=[CH:16][C:3]=1[CH2:4][NH:5][C:6]1[C:7]([NH2:13])=[CH:8][C:9]([I:12])=[CH:10][CH:11]=1

Participants

8

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 118113984N-(2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-4-iodo-2-nitroaniline

Product 1

HCID 118389318N1-(2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-4-iodobenzene-1,2-diamineYield 101%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 62662Ferrous sulfate heptahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-4-iodo-2-nitroaniline (0.38 g, 0.70 mmol) in tetrahydrofuran (10 mL), methanol (5 mL), and water (1 mL) was added ammonium chloride (0.30 g, 5.64 mmol) and iron (II) sulfate heptahydrate (0.69 g, 2.47 mmol). The bright orange suspension was treated with zinc (0.16 g, 2.47 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 reaction mixture was allowed to cool to room temperature. The mixture was filtered through Celite, and the filtercake was washed with chloroform (250 mL). The filtrate was washed with 5N ammonium hydroxide solution (75 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated to afford 0.36 g (100%) of N1-(2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-4-iodobenzene-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 chloroform (250 mL)
  4. washThe filtrate was washed with 5N ammonium hydroxide solution (75 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-078598fcb9f0488cad483b883915ef78
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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