HCID 118366172, compound → HCID 53418010, compound

HRID 59900Notes

Reaction equation

HRID 59900 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=1

Participants

4

Reactant 1

HCID 118366172HCID 118366172, compound

Product 1

HCID 53418010HCID 53418010, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(azidomethyl)picolinate (280 mg, 1.36 mmol) in methanol (20 mL) was added 10% Pd/C (50 mg). The mixture was stirred under 35 psi H2 for 2 hours. The reaction mixture was filtered through Celite, concentrated, and purified via column chromatography to provide methyl 4-(aminomethyl)picolinate (150 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-4e36260783d2446ba23ca2f0a74242fa
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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