Acetic Anhydride → HCID 59145586, compound

HRID 919100Notes

Reaction equation

HRID 919100 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=O.CC(OC(C)=O)=O>>[CH2:16]([O:15][C:11](=[O:14])/[CH:12]=[CH:1]/[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)[CH3:17]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 70211Ethyl oxoacetateHCID 1378606-Methylnicotinic acid

Product 1

HCID 59145586HCID 59145586, compoundYield 145.7%

Conditions

Temperature
130 °C

Procedure

6-Methylnicotinic acid (5 g, 36 mmol) and ethyl glyoxalate (50% solution in toluene—8.7 mL, 44 mmol) were added to Ac2O (25 mL) and stirred under a nitrogen atmosphere. The reaction was heated at 130° C. for 3 h then allowed to cool to RT over 17 h. The reaction was then quenched with water (10 mL) and concentrated to dryness in vacuo to afford the product as a brown solid (11.6 g, >100%). m/z=222 [M+H]+.

Workup

  1. temperatureto cool to RT over 17 h
  2. customThe reaction was then quenched with water (10 mL)
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-85a58aab8699432ab17fdc7ecc374804
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

Loading…