O-Xylene → 2-Acetamidopyridine

HRID 1679260Notes

Reaction equation

HRID 1679260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C1(C)C(C)=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>O>[C:16]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7918Acetic AnhydrideHCID 104392-Aminopyridine

Product 1

HCID 729292-Acetamidopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To 70.5 g. of 2-aminopyridine, partially dissolved in 180 g. of xylene, was slowly added, with stirring, 79.6 g. acetic anhydride. The addition was carried out over a 20-minute period. The reaction vessel was water-cooled so as to maintain the reaction mixture at 30-40° C during the addition. The reaction solution was then heated for 1 hour at a temperature of 74°-78° C to give 2-acetamidopyridine, which was used without isolation.

Workup

  1. additionThe addition
  2. waitwas carried out over a 20-minute period
  3. temperaturecooled so as
  4. additionduring the addition
  5. temperatureThe reaction solution was then heated for 1 hour at a temperature of 74°-78° C

Sources & evidence

ORD record
ord-0fa5bf02d8c5456c9f49beef9ca713b6
Source dataset
uspto-grants-1978_03
Patent number
US04080329

Reaction notes

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