Iodine → Ethyl 4,6-dichloro-3-iodo-1H-indole-2-carboxylate

HRID 440378Notes

Reaction equation

HRID 440378 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2.[OH-].[Na+].[I:19]I>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[C:4]([I:19])=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 2736407ethyl 4,6-dichloro-1H-indole-2-carboxylate

Product 1

HCID 15814285Ethyl 4,6-dichloro-3-iodo-1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 4,6-dichloro-indole-2-carboxylic acid, ethyl ester (5.2 g, 20.0 mmol) and sodium hydroxide (0.80 g, 20 mmol) in ethanol (250 mL). Add iodine (5.1 g, 20.0 mmol) as a solution in ethanol (100 mL). After 1 hour, concentrate the reaction mixture in vacuo to obtain a residue. Dissolve the residue in ethyl acetate and extract with 1M hydrochloric acid solution and then with saturated sodium chloride solution. Dry the organic layer over magnesium sulfate and evaporate in vacuo. Chromatograph on silica gel eluting with 25% ethyl acetate/hexane. Combine the product containing fractions and evaporate in vacuo. Recrystallize form ethyl acetate/hexane to give the title compound as a solid; mp: 218°-220° C. Elem. Anal. calculated for C11H8Cl2INO2 : C, 34.41; H, 2.10; N, 3.65. Found: C, 34.67; H, 2.09; N, 3.68.

Workup

  1. concentrationconcentrate the reaction mixture in vacuo
  2. customto obtain a residue
  3. extractionextract with 1M hydrochloric acid solution
  4. dry with materialDry the organic layer over magnesium sulfate
  5. customevaporate in vacuo
  6. additioncontaining fractions
  7. customevaporate in vacuo
  8. customRecrystallize
  9. customform ethyl acetate/hexane

Sources & evidence

ORD record
ord-cb1baf95815e4de4b675ba97fe9fa680
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Reaction notes

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