Methyl 4-iodo-2-nitrobenzoate → Methyl 2-amino-4-iodobenzoate

HRID 2387963Notes

Reaction equation

HRID 2387963 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-])=O)[CH:3]=1>C(Cl)Cl.CCOC(C)=O>[NH2:12][C:4]1[CH:3]=[C:2]([I:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 58476577Methyl 4-iodo-2-nitrobenzoate

Product 1

HCID 18929930Methyl 2-amino-4-iodobenzoateYield 90.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-iodo-2-nitrobenzoate (2.3 g, 7.4 mmol) in DCM (5 mL) and EtOAc (5 mL) was added SnCl2-2H2O (10.8 g, 89.7 mmol). The mixture was allowed to stir for 12 h at rt. The solvents were evaporated, and the residue was partitioned between 200 mL of saturated aqueous NaHCO3 and 200 mL of DCM. The organic solution was separated and the aqueous solution was extracted with DCM (2×100 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give methyl 2-amino-4-iodobenzoate (1.85 g, 90%).

Workup

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between 200 mL of saturated aqueous NaHCO3 and 200 mL of DCM
  3. customThe organic solution was separated
  4. extractionthe aqueous solution was extracted with DCM (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2c1ac8276de94c7b968f3017784e6cc0
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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