Water → HCID 13371549, compound

HRID 745766Notes

Reaction equation

HRID 745766 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].O.S(=O)(=O)(O)O.[I:26](O)(=O)=O>C(O)(=O)C.II>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([I:26])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 24345Iodic acidHCID 12795657HCID 12795657, compound

Product 1

HCID 13371549HCID 13371549, compoundYield 289.2%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

5.08 g of 4-methyl-β-carboline-3-carboxylic acid ethyl ester is dissolved in 40 ml of glacial acetic acid and combined with 0.96 ml of water, 0.24 ml of concentrated sulfuric acid, 688 mg of iodic acid, and 1.768 mg of iodine. The mixture is heated to 80° C. for 3 hours. After cooling, the mixture is suctioned off from undissolved material, and the filtrate is evaporated. The residue is taken up in ethanol/water. The thus-formed crystals are suctioned off, taken up in 500 ml of ethyl acetate, and extracted by stirring with 200 ml of 1N sodium hydroxide solution for 15 minutes. The organic phase is separated, concentrated by evaporation, the residue is extracted by stirring in ethyl acetate, and vacuum-filtered, thus obtaining 4.3 g of 6-iodo-4-methyl-β-carboline-3-carboxylic acid ethyl ester, mp 250°-255° C.

Workup

  1. temperatureAfter cooling
  2. customthe filtrate is evaporated
  3. extractionextracted
  4. customThe organic phase is separated
  5. concentrationconcentrated by evaporation
  6. extractionthe residue is extracted
  7. stirringby stirring in ethyl acetate
  8. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-278be343a5784a428300fb6872fe99bd
Source dataset
uspto-grants-1986_07
Patent number
US04600715

Reaction notes

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