Acetic Anhydride → HCID 13345321, compound

HRID 1584886Notes

Reaction equation

HRID 1584886 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[C:5]([C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>ClCCl>[CH3:1][C:2]1[N:7]=[C:6]2[C:8]([O:13][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5425676-Methyl-2,3-pyridinedicarboxylic acid

Product 1

HCID 13345321HCID 13345321, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-methylpyridine-2,3-dicarboxylic acid (19.75 g) and acetic anhydride (51 ml) was stirred and heated in an oil bath (bath temperature 110° C.) for 5 hours. The solvent was removed in vacuo and a 2:1 mixture of dichloromethane and ether was added, giving a dark brown solid. A solution of this solid in dichloromethane was passed through a pad of silica gel, eluting with dichloromethane, and the solvent was then evaporated to give partially purified 6-methylpyridine-2,3-dicarboxylic acid anhydride (12.1 g).

Workup

  1. customThe solvent was removed in vacuo
  2. additiona 2:1 mixture of dichloromethane and ether
  3. additionwas added
  4. customgiving a dark brown solid
  5. washeluting with dichloromethane
  6. customthe solvent was then evaporated

Sources & evidence

ORD record
ord-1f001ef2cea64ac6a0ed426e344da9d3
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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