Methyl 3-benzyloxy-6-methoxypicolinate → Methyl 3-hydroxy-6-methoxypicolinate

HRID 350657Notes

Reaction equation

HRID 350657 reaction equation
C([O:8][C:9]1[C:10]([C:17]([O:19][CH3:20])=[O:18])=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].CO>[OH:8][C:9]1[C:10]([C:17]([O:19][CH3:20])=[O:18])=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 22175139Methyl 3-benzyloxy-6-methoxypicolinateHCID 178418361HCID 178418361, compound

Product 1

HCID 17817640Methyl 3-hydroxy-6-methoxypicolinateYield 76%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% palladium-carbon (48 mg) was added to 480 mg of methyl 3-benzyloxy-6-methoxy-picolinate. After the replacement of the atmosphere by nitrogen, 25 ml of methanol was added thereto. Further, after the replacement of the atmosphere by hydrogen, the mixture was vigorously stirred to allow a reaction to proceed. One hr after the initiation of the reaction, the reaction mixture was filtered, followed by purification by chromatography on silica gel (chloroform-methanol) to give 240 mg (yield 76%) of the title compound.

Workup

  1. customa reaction
  2. customOne hr after the initiation of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customfollowed by purification by chromatography on silica gel (chloroform-methanol)

Sources & evidence

ORD record
ord-9d1c60bdc1104c388a75202f1dc0a57f
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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