Sodium Iodide → HCID 70424592, compound

HRID 1903113Notes

Reaction equation

HRID 1903113 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]=1COC)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])C.[I-:22].[Na+].[CH3:24][Si](C)(C)Cl>C(#N)C>[CH3:1][O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:24])[C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[I:22])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 13041786HCID 13041786, compound

Product 1

HCID 70424592HCID 70424592, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 1.5 g of 4-methoxymethyl-beta-carboline-3-carboxylic-acid-ethylester, 20 ml of acetonitrile, 3.1 g of sodium iodide and 2.7 ml of trimethylchlorosilane is stirred at 60° C. for 2 h. After cooling, it is poured into ice water and extracted with ethyl acetate. The extracts are washed with saturated sodium thiosulfate solution, dried and concentrated. 1.65 g of 4-iodo-methyl-beta-carboline-3-carboxylic-acid-methylester with a m.p. of 280°-286° C. is obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with saturated sodium thiosulfate solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a09bdfce7fb94d089e727100d33c3390
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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