Hydrochloric Acid → HCID 58447740, compound

HRID 1036287Notes

Reaction equation

HRID 1036287 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]CC)=[O:16])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58447698Ethyl 2-(2'-fluoro-2,4'-bipyridin-5-yl)acetate

Product 1

HCID 58447740HCID 58447740, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of ethyl 2-(2′-fluoro-2,4′-bipyridin-5-yl)acetate 208-2 (93 mg, 0.36 mmol) and NaOH (57 mg, 1.43 mmol) in THF (0.5 mL) and water (0.5 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 portion was concentrated to give 2-(2′-fluoro-2,4′-bipyridin-5-yl)acetic acid 208-3 as pale white solid. MS m/z 233.1 (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. concentrationThe organic portion was concentrated

Sources & evidence

ORD record
ord-6021ddb99ec14aab8ee3a1bb35138937
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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