Acetic Acid → HCID 13345321, compound

HRID 1011333Notes

Reaction equation

HRID 1011333 reaction equation
[CH3:1][C:2]1[N:7](C(O)=O)[CH:6]([C:11]([OH:13])=[O:12])[CH:5]=[CH:4][CH:3]=1.[C:14](O)(=[O:16])C.N1C=CC=CC=1.CCCCCC>COCCOC.CCOCC>[CH3:1][C:2]1[N:7]=[C:6]2[C:11](=[O:12])[O:13][C:14](=[O:16])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8058HexaneHCID 67315455HCID 67315455, compound

Product 1

HCID 13345321HCID 13345321, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 6-methyl-1,2-pyridine dicarboxylic acid (25 g, 138 mmol) and acetic acid (42 mL, 733 mmol) in DME (150 mL) is treated with pyridine (22 mL, 272 mmol) and stirred at room temperature for 2 h. The pale yellow solution is diluted with ether (250 mL) and then hexane (1250 mL) is added slowly. A white precipitate is formed. The solution is cooled to 0° C. for 30 min and the white solid is collected by filtration. The solid is washed with hexane and dried to give the title compound as a white solid (16.7 g, 74%).

Workup

  1. customA white precipitate is formed
  2. temperatureThe solution is cooled to 0° C. for 30 min
  3. filtrationthe white solid is collected by filtration
  4. washThe solid is washed with hexane
  5. customdried

Sources & evidence

ORD record
ord-0696e96a5a6847609df9f444b7c2846a
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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