Hydrochloric Acid → HCID 90389323, compound

HRID 1526624Notes

Reaction equation

HRID 1526624 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1)#[C:2][CH3:3].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)#[C:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90389419HCID 90389419, compound

Product 1

HCID 90389323HCID 90389323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(prop-1-yn-1-yl)picolinate (0.18 g, 1.05 mmol) in tetrahydrofuran (3.48 ml) was added sodium hydroxide 1.0 N solution (1.05 mL, 1.045 mmol, Sigma). The reaction was stirred for 1.5 hours at room temperature. Hydrogen chloride (4.0M solution in 1,4-dioxane; 0.26 ml, 1.05 mmol, Sigma Aldrich) was added and the reaction stirred for an additional 10 minutes. The reaction was concentrated in vacuo to provide 5-(prop-1-yn-1-yl)picolinic acid as a light yellow solid. The material was used without further purification assuming theoretical yield. MS m/z [M+H]+=162.1. Calculated from C9H7NO2: 161.157

Workup

  1. stirringthe reaction stirred for an additional 10 minutes
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-96adcc5b84bd4fbb950ba5d44b22659d
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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