Methyl 5-(benzyloxy)picolinate → Methyl 5-hydroxypyridine-2-carboxylate

HRID 443441Notes

Reaction equation

HRID 443441 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11]CC2C=CC=CC=2)=[CH:7][N:6]=1)=[O:4]>[Pd].C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 15574702Methyl 5-(benzyloxy)picolinate

Product 1

HCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7.9 g of 5-benzyloxy-2-pyridinecarboxylic acid methyl ester, 100 ml of 75% aqueous ethanol and 0.2 g of palladium over carbon (5%) is hydrogenated at 47 psi at room temperature. After the theoretical uptake of hydrogen, the mixture is filtered and the filtrate evaporated to yield 5-hydroxy-2-pyridinecarboxylic acid methyl ester melting at 191.5°-192.5°.

Workup

  1. customis hydrogenated at 47 psi at room temperature
  2. filtrationAfter the theoretical uptake of hydrogen, the mixture is filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-0f5841e7dcc0483ab95f6c211d99aa3a
Source dataset
uspto-grants-1981_04
Patent number
US04260620

Reaction notes

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