Ammonium Hydroxide → HCID 19851786, compound

HRID 34924Notes

Reaction equation

HRID 34924 reaction equation
[N:1]1[C:10]2[CH:9]([CH2:11][CH2:12][CH2:13][N:14]3[C:18]4=[N:19][CH:20]=[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)[CH:22]=[C:17]4N=N3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-:30].[NH4+]>O>[N:1]1[C:10]2[CH:9]([CH2:11][CH2:12][CH2:13][NH:14][C:18]3[C:17]([OH:30])=[CH:22][C:21]([CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][N:19]=3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 198517953-(5,6,7,8-Tetrahydroquinol-8-yl)propyl-6-(pyrid-3-ylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine

Product 1

HCID 19851786HCID 19851786, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[3-(5,6,7,8-tetrahydroquinol-8-yl)propyl]-6-(pyrid-3-ylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine (3.56 g) and polyphosphoric acid (17.5 g) were heated with stirring at 188°-197° C. for 50 minutes. Water (30 ml) was added to the hot residue and, after slight cooling, the solution was basified with aqueous ammonium hydroxide to pH 10 and then extracted with chloroform. The combined chloroform extracts were dried over magnesium sulphate, concentrated in vacuo and the residue was chromatographed on silica eluted with 5% v/v methanol in chloroform to give the title compound as a brown gum (0.68 g). The aqueous portion after extraction, was concentrated to dryness, to give a paste, water (100 ml) was then added, the mixture was refluxed for 1 hour and a brown oil which formed was extracted with chloroform (3×100 ml). The extracts were dried, combined and concentrated to give a further quantity of the title compound as an oil (0.31 g). The two portions of the product were combined, converted to the trihydrochloride with ethanolic HCl and then recrystallised, first from isopropanol and then from isopropanol/methanol to give the title compound as a buff solid (0.5 g).

Workup

  1. temperaturewere heated
  2. extractionextracted with chloroform
  3. dry with materialThe combined chloroform extracts were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue was chromatographed on silica
  6. washeluted with 5% v/v methanol in chloroform

Sources & evidence

ORD record
ord-91d464203cf341018a83e7f99c8e3e52
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Reaction notes

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