Methyl 5-(3-fluorobenzyl)picolinate → 5-(3-Fluorobenzyl)picolinic acid

HRID 1777540Notes

Reaction equation

HRID 1777540 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=1>[OH-].[Na+].C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1

Participants

4

Reactant 1

HCID 67974406Methyl 5-(3-fluorobenzyl)picolinate

Product 1

HCID 679745615-(3-Fluorobenzyl)picolinic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 5-(3-fluorobenzyl)picolinate (0.149 g; 0.607 mmol) in NaOH 2M (2 mL) and ethanol (2 mL) was stirred at room temperature for 2 hours and then evaporated to dryness. The residue was dissolved in water and acidified to pH 2 with a 6N solution of hydrochloric acid in water. The mixture was extracted with ethyl acetate and the combined organic layers were dried and concentrated under reduced pressure. The crude material was used in the next step without any further purification.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe combined organic layers were dried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was used in the next step without any further purification

Sources & evidence

ORD record
ord-b43cb26339cc4aaa9b467cb2df83bf7a
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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