Stannous Chloride → Methyl 3-amino-4-hydroxy-5-iodobenzoate

HRID 14184

Reaction equation

HRID 14184 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[I:15].[Sn](Cl)Cl>C(O)C>[NH2:12][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([I:15])[C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 21086206Methyl 4-hydroxy-3-iodo-5-nitrobenzoate

Product 1

HCID 21086158Methyl 3-amino-4-hydroxy-5-iodobenzoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75.

Workup

  1. temperatureat reflux
  2. customquenched by saturated potassium carbonate (100 mL)
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. extractionthe filtrate was extracted with ethyl acetate (4×100 mL)
  5. dry with materialThe combined organic extracts were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e96ad27d31df4539833bb9453bfc15bb
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

Loading…