Hydrochloric Acid → HCID 10448391, compound

HRID 1676974Notes

Reaction equation

HRID 1676974 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([I:11])[CH:9]=2)[NH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl.O>C(O)C.[Zn]>[I:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 10950273Ethyl 3,5-diiodo-1H-indole-2-carboxylate

Product 1

HCID 10448391HCID 10448391, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 702EthanolSolvent

Procedure

Ethyl 3,5-diiodo-1H-indole-2-carboxylate (12.1 g, 26.4 mmol) was suspended in 250 mL of absolute ethanol, to which concentrated aqueous hydrogen chloride (22.0 mL, 264 mmol) was added. Zinc dust (17.3 g, 264 mmol) was added portionwise over 30 minutes. After stirring for 45 minutes, two additional portions of zinc were added slowly (5.2 and 4.4 g, 146 mmol). After stirring for 30 minutes, the mixture was poured into water and extracted four times with ethyl acetate. The combined organic extracts were washed once with aqueous saturated NaHCO3 and once with aqueous saturated NaCl. The organic extract was dried with Na2SO4, filtered and concentrated in vacuo. The residue was crystallized three times from hexanes and ethyl acetate, providing the title compound. The mother liquor was columned by flash chromatography (0 to 8% ethyl acetate in hexanes) to provide an additional amount of the title compound. HRMS (ES) exact mass calculated for C11H10INO2 (M+Na+): 377.9648. Found 377.9649.

Workup

  1. additionwas added
  2. stirringAfter stirring for 30 minutes
  3. extractionextracted four times with ethyl acetate
  4. washThe combined organic extracts were washed once with aqueous saturated NaHCO3 and once with aqueous saturated NaCl
  5. extractionThe organic extract
  6. dry with materialwas dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized three times from hexanes and ethyl acetate

Sources & evidence

ORD record
ord-3acc29913b0f4457b42a662f81f91838
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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