Hydrochloric Acid → 2-(Methoxycarbonyl)-6-methylisonicotinic acid

HRID 2071154Notes

Reaction equation

HRID 2071154 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[CH:4]=1)=[O:2].[OH:14]OS([O-])=O.[K+].Cl.O>CN(C=O)C>[CH3:13][O:12][C:10]([C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([CH3:9])[N:6]=1)[C:1]([OH:14])=[O:2])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 72213904Methyl 4-formyl-6-methylpicolinate

Product 1

HCID 595708792-(Methoxycarbonyl)-6-methylisonicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 216 mg (1.20 mmol) of methyl 4-formyl-6-methylpicolinate in 4 mL of DMF was added 790 mg (1.29 mmol) of Oxone. After about 2 h, 5 mL of 1N HCl and 5 mL of H2O were added, and the aqueous layer was extracted with EtOAc (3×). The combined extracts were dried over Na2SO4, filtered, and concentrated. The desired product (2-(methoxycarbonyl)-6-methylisonicotinic acid) was used in the next reaction without further purification.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (3×)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe desired product (2-(methoxycarbonyl)-6-methylisonicotinic acid) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-6fc7316ec200423f8fac867276f238b5
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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