Aniline → HCID 178420746, compound

HRID 868498Notes

Reaction equation

HRID 868498 reaction equation
NC1C=CC=CC=1.Cl[C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[CH:16]=[N:17][C:10]=12.C(Cl)(Cl)Cl.CO>O>[N:17]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][CH:9]=2)[NH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6115Aniline3×HCID 13384764HCID 13384764, compoundHCID 21584188Chloroform methanol

Product 1

HCID 178420746HCID 178420746, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Aniline (1.6 g, 17.5 mMol) and 1.0 g (3.5 mMol) 7-chloro-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine were suspended in 100 mL water and heated at 100° C. oil bath for two days. The oil bath temperature was raised to 130° C. and the reaction was continued for two days, when 2 equivalents of aniline were added. On the tenth day of heating, 5 equivalents of aniline were added and the reaction continued for six hours more. The mixture was concentrated in vacuo to give a dark oil. Chromatography twice on silica gel using CHCl3 /CH3OH (9:1) gave nearly pure 7-anilino-3-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine. This was crystallized in two batches from methanol. Total yield was 0.307 g, 18%; m.p. 186°-187° C. The NMR, UV and HPLC retention time were identical to the product prepared enzymatically.

Workup

  1. temperatureThe oil bath temperature was raised to 130° C.
  2. temperatureOn the tenth day of heating
  3. waitthe reaction continued for six hours
  4. concentrationThe mixture was concentrated in vacuo
  5. customto give a dark oil

Sources & evidence

ORD record
ord-d429c4182ab04a05b29147f005c90b62
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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