p-Toluenesulfonic acid → HCID 12354096, compound

HRID 1658502Notes

Reaction equation

HRID 1658502 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.CC[O:24][C:25]([CH:27]1[C:31](=O)[CH2:30][CH2:29][CH2:28]1)=O>>[O:24]=[C:25]1[N:10]2[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]2=[N:1][C:28]2[CH2:29][CH2:30][CH2:31][C:27]1=2

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 729302-Aminonicotinic acid

Product 1

HCID 12354096HCID 12354096, compound

Procedure

A mixture of 5.0 g of 2-aminonicotinic acid, 0.4 g. p-toluenesulfonic acid, and 25 ml of ethyl cyclopentanone-2-carboxylate is stirred magnetically and immersed in an oil bath preheated to 125°. The temperature of the oil bath is gradually raised and reaches 170° in 23 minutes. A clear solution occurs in 55 minutes when the oil bath temperature reaches 178° and 4.0 ml of distillate is collected in a Dean-Stark trap. The product crystallizes from the cooled reaction mixture. The filtered, air-dried product weighs 6.2 g., m.p. 187°-192°. Recrystallization from 100 ml of toluene gives 4.91 g of product, m.p. 189°-193°.

Workup

  1. customimmersed in an oil bath
  2. custompreheated to 125°
  3. temperatureThe temperature of the oil bath is gradually raised
  4. waitA clear solution occurs in 55 minutes
  5. customreaches 178°
  6. distillation4.0 ml of distillate is collected in a Dean-Stark trap
  7. customThe product crystallizes from the cooled reaction mixture
  8. customRecrystallization from 100 ml of toluene

Sources & evidence

ORD record
ord-5d3dae92c71a496cb619d13aea4776d7
Source dataset
uspto-grants-1976_06
Patent number
US03965100

Reaction notes

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