Methyl 3-iodo-4-methyl-5-nitrobenzoate → HCID 67512060, compound

HRID 446222Notes

Reaction equation

HRID 446222 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([CH3:13])=[C:6]([I:14])[CH:5]=1>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([I:14])[C:7]([CH3:13])=[C:8]([NH2:10])[CH:9]=1

Participants

4

Reactant 1

HCID 24728110Methyl 3-iodo-4-methyl-5-nitrobenzoate

Product 1

HCID 67512060HCID 67512060, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-iodo-4-methyl-5-nitro-benzoic acid methyl ester (2.0 g, 6.23 mmol) in a mixture of THF (40 mL) and methanol (1 mL) was added SnCl2 dihydrate (4.22 g, 18.69 mmol). The reaction mixture was stirred at 60° C. for six hours, then cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 1.22 g (67%) of 3-amino-5-iodo-4-methyl-benzoic acid methyl ester.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bef56ea76a9e4329a92f0b056443b44b
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Reaction notes

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