Hydrochloric Acid → 2-Phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

HRID 60141Notes

Reaction equation

HRID 60141 reaction equation
Cl.CO.[C:4]1([C:10]2[N:21]=[C:13]3[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][N:12]3[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>[C].[Pd].C(Cl)Cl>[C:4]1([C:10]2[N:21]=[C:13]3[CH2:14][CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17][N:12]3[N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 825667812-Phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 825678132-Phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acidYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

10% Palladium-carbon (3 g) and concentrated hydrochloric acid (3.1 ml) were added to a mixed solution of methanol (200 ml) and methylene chloride (150 ml) containing the 2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid (3 g) obtained in (Example 3.18) <Step 4>, and the obtained mixture was then stirred in a hydrogen atmosphere for 15 hours. Thereafter, the reaction solution was heated to 40° C., and then, it was further stirred for 4 hours. Thereafter, the reaction solution was filtered with Celite, and was then washed with methanol. The filtrate was concentrated under reduced pressure, and the solvent was then distilled away. After that, methanol (20 ml) and a 4 N sodium hydroxide aqueous solution (9 ml) were added to the residue, and the obtained mixture was then stirred at 50° C. for 30 minutes. Thereafter, the solvent was distilled away under reduced pressure, and a 1 N hydrochloric acid aqueous solution (9 ml) was then added to the residue. The generated solid was collected by filtration, and was then washed with water (10 ml). The obtained solid was dried under reduced pressure at 45° C. for 15 hours, so as to obtain the title compound (2.4 g) in the form of a white solid.

Workup

  1. customobtained in (Example 3.18) <Step 4>
  2. filtrationThereafter, the reaction solution was filtered with Celite
  3. washwas then washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. distillationthe solvent was then distilled away
  6. additionAfter that, methanol (20 ml) and a 4 N sodium hydroxide aqueous solution (9 ml) were added to the residue
  7. stirringthe obtained mixture was then stirred at 50° C. for 30 minutes
  8. distillationThereafter, the solvent was distilled away under reduced pressure
  9. additiona 1 N hydrochloric acid aqueous solution (9 ml) was then added to the residue
  10. filtrationThe generated solid was collected by filtration
  11. washwas then washed with water (10 ml)
  12. customThe obtained solid was dried under reduced pressure at 45° C. for 15 hours

Sources & evidence

ORD record
ord-d6dd5d872ca640188fdd7be4e6b80fc9
Source dataset
uspto-grants-2016_09
Patent number
US09440970B2

Reaction notes

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