2-Pyridinecarboxaldehyde → HCID 272148, compound

HRID 1414867Notes

Reaction equation

HRID 1414867 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]=O.N1CCCC1>CO>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 31268PyrrolidineHCID 321710Oxindole

Product 1

HCID 272148HCID 272148, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of oxindole (37.5 g, 0.28 mole), pyridine2-carboxaldehyde (31.8 g, 0.29 mole) and pyrrolidine (21 ml) in 90 ml of methanol is heated on a steam bath. Within a short time an exothermic reaction occurs, resulting in the deposition of a thick solid mass. The solids are collected, washed with methanol and recrystallized from methanol to give 52.5 g of product: m.p. 204°-205°.

Workup

  1. temperatureis heated on a steam bath
  2. customWithin a short time an exothermic reaction
  3. customresulting in the deposition of a thick solid mass
  4. customThe solids are collected
  5. washwashed with methanol
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5693a7c849304ab58a1b7fb41838725e
Source dataset
uspto-grants-1977_01
Patent number
US04002749

Reaction notes

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