Hydrochloric Acid → 2-(2',3-Dimethyl-2,4'-bipyridin-5-yl)acetic acid

HRID 592185Notes

Reaction equation

HRID 592185 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH:15](C(OCC)=O)[C:16]([O:18]CC)=[O:17])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][C:16]([OH:18])=[O:17])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58447640Diethyl 2-(2',3-dimethyl-2,4'-bipyridin-5-yl)malonate

Product 1

HCID 584477082-(2',3-Dimethyl-2,4'-bipyridin-5-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of diethyl 2-(2′,3-dimethyl-2,4′-bipyridin-5-yl)malonate 156-4 (935 mg, 3 mmol) and NaOH (480 mg, 12 mmol) in THF (1.8 mL) and water (1.8 mL) was stirred at 65° C. for 3 hours. After cooled down to room temperature, the mixture was treated with 3N HCl aqueous solution to adjust the pH around 3, 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′,3-dimethyl-2,4′-bipyridin-5-yl)acetic acid 156-5 as white solid. MS m/z 243.1 (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-b05bfbf23f204760a04af377bca8a1ec
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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