Methyl 2-iodo-3-nitrobenzoate → Methyl 3-amino-2-iodobenzoate

HRID 1639833

Reaction equation

HRID 1639833 reaction equation
[I:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>[Ni].C(OCC)(=O)C>[NH2:12][C:11]1[C:2]([I:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 264093Methyl 2-iodo-3-nitrobenzoate

Product 1

HCID 18340005Methyl 3-amino-2-iodobenzoateYield 86.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-iodo-3-nitrobenzoate (77.0 g, 251 mmol) and a catalytic amount of Raney nickel in ethyl acetate (100 mL) was stirred under hydrogen atmosphere at room temperature for 2 days, and filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10) to give the title compound (60.0 g, yield 86%).

Workup

  1. filtrationfiltered through celite
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-ce1864c71942400885a878c44086a9e2
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Linked notes

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