Hydrochloric Acid → HCID 58447767, compound

HRID 1036306Notes

Reaction equation

HRID 1036306 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH2:14][C:15]([O:17]C)=[O:16])[CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58447776HCID 58447776, compound

Product 1

HCID 58447767HCID 58447767, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-(2′-methyl-2,4′-bipyridin-4-yl)acetate 238-2 (621 mg, 2.56 mmol) and NaOH (409 mg, 10.24 mmol) in 1,4-dioxane (6 mL) and water (6 mL) was stirred at 80° C. for 3 hours. After cooled down to room temperature, the mixture was treated with 3N HCl aqueous solution to adjust the pH to around 4, and then stirred for 15 minutes. The resulting solution was evaporated to dryness and the remaining solid was extracted with 20% methanol in ethyl acetate. The organic extraction was concentrated to give 2-(2′-methyl-2,4′-bipyridin-4-yl)acetic acid 238-3 as pale white solid. MS m/z 229.1 (M+1).

Workup

  1. temperatureAfter cooled down to room temperature
  2. stirringstirred for 15 minutes
  3. customThe resulting solution was evaporated to dryness
  4. extractionthe remaining solid was extracted with 20% methanol in ethyl acetate
  5. extractionThe organic extraction
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-d7267a46bddc4601b631c05c7296365d
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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