Stannous Chloride → Ethyl 3-amino-4-iodobenzoate

HRID 40057Notes

Reaction equation

HRID 40057 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)[CH3:2].[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[I:11])[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 11186300Ethyl 4-iodo-3-nitrobenzoate2×

Product 1

HCID 59762281Ethyl 3-amino-4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of ethyl4-iodo-3nitrobenzoate (Compound 30, 9.45 g, 29.4 mmol) in ethyl acetate (200 ml) and tin(II) chloride dehydrate (33.1 g, 147 mmol). Reaction was heated to 85° C. for 1 h, cooled to 25° C., quenched with NaHCO3(S), filtered off white solid, and then organic layer was concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a light yellow solid.

Workup

  1. customReaction
  2. temperaturecooled to 25° C.
  3. customquenched with NaHCO3(S)
  4. filtrationfiltered off white solid
  5. concentrationorganic layer was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-35f49d8aefe741fda95c056310933327
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

Loading…