Hydrochloric Acid → HCID 57475876, compound

HRID 627709Notes

Reaction equation

HRID 627709 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.[OH-].[K+].O.Cl>CO>[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 68446117HCID 68446117, compound

Product 1

HCID 57475876HCID 57475876, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a small flask were added methyl 5-(cyclopropylethynyl)picolinate (240 mg, 1.193 mmol) and potassium hydroxide (147 mg, 2.62 mmol) in MeOH (4 ml). The mixture was stirred at 50° C. for 20 min. It was cooled to RT and the solvent was reduced. The white solid was treated with small amount of water (˜1.5 mL), and acidified by 6N HCl to pH 2. The light brown precipitate was formed and the resulting mixture was cooled to 0° C. by ice bath. The brown precipitate was collected by filtration to yield 5-(cyclopropylethynyl)picolinic acid (163 mg, 0.871 mmol, 73.0% yield) as light yellow solid. It was dried in high vacuum for overnight and was used directly for next step. MS m/z=188.1 (M+H).

Workup

  1. temperatureIt was cooled to RT
  2. customThe light brown precipitate was formed
  3. temperaturethe resulting mixture was cooled to 0° C. by ice bath
  4. filtrationThe brown precipitate was collected by filtration

Sources & evidence

ORD record
ord-d83a8bd551604f4bbe90a7d674e6b5ed
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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