Methyl 4-amino-3-iodo-5-nitrobenzoate → Methyl 3,4-diamino-5-iodobenzoate

HRID 446226

Reaction equation

HRID 446226 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([I:14])[CH:5]=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([I:14])[C:7]([NH2:13])=[C:8]([NH2:10])[CH:9]=1

Participants

3

Reactant 1

HCID 67512142Methyl 4-amino-3-iodo-5-nitrobenzoate

Product 1

HCID 67512100Methyl 3,4-diamino-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-amino-3-iodo-5-nitro-benzoic acid methyl ester in ethyl acetate (50 mL) was added SnCl2 dihydrate. The mixture was heated to 70° C. for two 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 to provide 1.68 g (quantitative) of 3,4-diamino-5-iodo-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

Sources & evidence

ORD record
ord-8b876b71f5914e3cb992a1c68db7bca0
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Linked notes

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