Stannous chloride dihydrate → 2-Amino-4-iodo-benzoic acid

HRID 2265200Notes

Reaction equation

HRID 2265200 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:11][C:4]1[CH:3]=[C:2]([I:1])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 189198834-Iodo-2-nitrobenzoic acid

Product 1

HCID 227247802-Amino-4-iodo-benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Iodo-2-nitro-benzoic acid (20 g, 68 mmol, 1.0 equiv.) was dissolved in 200 mL of EtOAc and then SnCl2.2H2O (46 g, 204 mmol, 3.0 equiv.) was added in three portions. The reaction mixture was stirred at rt for 16 h. Satd. aq. NaHCO3 was carefully added to adjust the mixture to pH=9. The precipitated solid was removed by filtration through diatomaceous earth, washing with water. The aqueous layer in the filtrate was separated and acidified with conc. HCl to pH=2. The precipitated solid was collected by filtration and dried to afford the title compound as white solid (19 g, 68 mmol, 100%). 1H NMR (400 MHz, CD3OD): 1H NMR (500 MHz, CDCl3): 7.56 (d, J=8.5, 1H), 7.08 (s, 1H), 6.99 (d, J=8.5, 1H), 5.71 (br s, 2H).

Workup

  1. customThe precipitated solid was removed by filtration through diatomaceous earth
  2. washwashing with water
  3. customThe aqueous layer in the filtrate was separated
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-170b4e83f64741438b9fbf504f44b27b
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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