Ammonium formate → HCID 89666850, compound

HRID 2171249Notes

Reaction equation

HRID 2171249 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N:16]2[N:20]=[CH:19][CH:18]=[N:17]2)=[CH:14][C:13]([N+:21]([O-])=O)=[CH:12][N:11]=1>[Pd].CO.C(OCC)(=O)C>[CH3:5][O:6][CH2:7][CH2:8][O:9][C:10]1[N:11]=[CH:12][C:13]([NH2:21])=[CH:14][C:15]=1[N:16]1[N:20]=[CH:19][CH:18]=[N:17]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89666864HCID 89666864, compound

Product 1

HCID 89666850HCID 89666850, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

10% Pd/C (200 mg) and ammonium formate (200 mg) were added to an MeOH/ethyl acetate (5 ml/5 ml) solution containing 2-(2-methoxyethoxy)-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine (286 mg) obtained in the 1st step, followed by reflux for 1 hour. Insoluble matter was removed using Celite and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:5) and a white solid of 6-(2-methoxyethoxy)-5-(2H-1,2,3-triazol-2-yl)pyridin-3-amine (240 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. temperatureby reflux for 1 hour
  3. customInsoluble matter was removed
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:5)

Sources & evidence

ORD record
ord-dd25e7ddce6d42939fee9a0feef3475d
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…