Hydrochloric Acid → 6-Cyclopropylpicolinic acid

HRID 334045Notes

Reaction equation

HRID 334045 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:14][CH2:13]2)[N:7]=1)=[O:5])C.[Li+].[OH-].O.Cl>C1COCC1>[CH:12]1([C:8]2[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:11]=[CH:10][CH:9]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86688276Ethyl 6-cyclopropylpicolinate

Product 1

HCID 824151916-Cyclopropylpicolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (5.23 mmol) 6-cyclopropyl-pyridine-2-carboxylic acid ethyl ester was suspended in 10 mL THF and treated with 350 mg (14.6 mmol) LiOH and 5 mL water at RT for 2.5 h. The reaction mixture was acidified with 4 M aqueous hydrochlorid acid and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f026a0a8a7054ec9b08bc0fec01bdaf1
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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