Water → HCID 58802258, compound

HRID 2071160Notes

Reaction equation

HRID 2071160 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:6]([O:8][CH3:9])=[O:7].[OH2:14]>C(Cl)(Cl)(Cl)Cl.CC#N>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[C:11]([CH3:13])[N:12]=[C:3]([C:2]([OH:14])=[O:1])[CH:4]=1)=[O:7]

Participants

5

Reactant 2

HCID 962WaterHCID 67026976HCID 67026976, compound

Product 1

HCID 58802258HCID 58802258, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirring mixture of 51.6 mg (0.283 mmol) of methyl 2-(hydroxymethyl)-6-methylisonicotinate in 1.6 mL of CCl4, 1.6 mL of CH3CN, and 2.4 mL of H2O was added 348 mg (1.63 mmol) of NaIO4, and 8.8 mg (0.0424 mmol) of RuCl3.(H2O)n. After 2 h, 6 mg of RuCl3.(H2O)n was added, and after 2.5 h the mixture was filtered through Celite twice with EtOAc and MeOH. The solution was concentrated and then reconcentrated with MeOH (2×) to remove H2O. Crude 4-(methoxycarbonyl)-6-methylpicolinic acid was used in the next reaction without further purification.

Workup

  1. addition(H2O)n was added
  2. filtrationafter 2.5 h the mixture was filtered through Celite twice with EtOAc and MeOH
  3. concentrationThe solution was concentrated
  4. customto remove H2O
  5. customCrude 4-(methoxycarbonyl)-6-methylpicolinic acid was used in the next reaction without further purification

Sources & evidence

ORD record
ord-f91391d1d47a4f2585035374b1b5e68e
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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