Acetic Anhydride → HCID 89650047, compound

HRID 2174688Notes

Reaction equation

HRID 2174688 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([OH:12])=[O:11])[C:7]([C:13]([OH:15])=[O:14])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[C:16](OC(=O)C)(=O)C>>[CH3:16][O:11][C:10]([C:8]1[C:7]([C:13]([OH:15])=[O:14])=[CH:6][CH:5]=[C:4]([CH:1]2[CH2:2][CH2:3]2)[N:9]=1)=[O:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 20067183HCID 20067183, compound

Product 1

HCID 89650047HCID 89650047, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 6-cyclopropyl-pyridine-2,3-dicarboxylic acid (D82, 19.8 g, 95.6 mmol) in acetic anhydride (100 ml) was heated at 110° C. for 2 hours and then was concentrated in vacuum. To the residue was added methanol (100 ml) and stirring was continued at room temperature for 2 hours. The reaction mixture was concentrated in vacuum and the residue was purified by column chromatography on silica gel (10% ethyl acetate in petroleum ether) and C-18 reversed phase column (5% methanol/water to methanol) to give D83 (10.7 g) as a yellow solid.

Workup

  1. concentrationwas concentrated in vacuum
  2. additionTo the residue was added methanol (100 ml)
  3. concentrationThe reaction mixture was concentrated in vacuum
  4. customthe residue was purified by column chromatography on silica gel (10% ethyl acetate in petroleum ether) and C-18
  5. customto give D83 (10.7 g) as a yellow solid

Sources & evidence

ORD record
ord-a46ce382885a46fdb82d7f292af8e1b2
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

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