Hydrochloric Acid → HCID 44466336, compound

HRID 415492Notes

Reaction equation

HRID 415492 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[C:19](=[O:20])[N:9]2[CH:10]=[C:11]([C:14]([O:16]CC)=[O:15])[CH:12]=[CH:13][C:8]2=[N:7]1.O.[OH-].[Li+].Cl.ClCCl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[C:19](=[O:20])[N:9]2[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=[CH:13][C:8]2=[N:7]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 44466333HCID 44466333, compound

Product 1

HCID 44466336HCID 44466336, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 15-mL round-bottom flask ethyl 2-(3,4-dichlorobenzyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate (0.46 mmol) was dissolved in a mixture of THF (2 mL) and MeOH (2 mL). Lithium hydroxide monohydrate (0.93 mmol) was dissolved in water (2 mL) and added to the reaction flask dropwise. The reaction mixture was stirred at room temperature for 6 hours, and then acidified with 1N aqueous HCl. The resulting mixture containing precipitate was poured into a separatory funnel and dichloromethane added until all precipitate dissolved (200 mL). The resulting solution was washed with water (50 mL) and dried over MgSO4. Concentration yielded 2-(3,4-dichlorobenzyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid as light-yellow precipitate. The final compound is more soluble in chloroform than dichloromethane.

Workup

  1. additionadded to the reaction flask dropwise
  2. additionThe resulting mixture containing precipitate
  3. additionwas poured into a separatory funnel
  4. dissolutiondissolved (200 mL)
  5. washThe resulting solution was washed with water (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationConcentration

Sources & evidence

ORD record
ord-fa42c3c18c0c48bf8d937bbb8b96b16d
Source dataset
uspto-grants-2012_01
Patent number
US08088792B2

Reaction notes

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