2-Amino-3-methylpyridine → HCID 12354097, compound

HRID 1658501Notes

Reaction equation

HRID 1658501 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CC[O:11][C:12]([CH:14]1[C:18](=O)[CH2:17][CH2:16][CH2:15]1)=O>COCCO>[CH3:8][C:7]1[C:2]2=[N:1][C:15]3[CH2:16][CH2:17][CH2:18][C:14]=3[C:12](=[O:11])[N:3]2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 12354097HCID 12354097, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 10.8 g of 2-amino-3-picoline, 31.2 g of ethyl cyclopentanone-2-carboxylate, and 250 ml of ethylene glycol monomethyl ether is stirred and heated under reflux for 40 hours. The solution is concentrated as far as possible on a rotary evaporator. The residual oil crystallizes and is filtered with suction to give 14.15 g of air-dried solid. This is recrystallized from 425 ml of cyclohexane to give 11.3 g of product, after drying at 78°. The melting point is 100°-102°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 hours
  3. concentrationThe solution is concentrated as far as
  4. custompossible on a rotary evaporator
  5. customThe residual oil crystallizes
  6. filtrationis filtered with suction

Sources & evidence

ORD record
ord-349ef6598ebe4665bdff05f84b96fc05
Source dataset
uspto-grants-1976_06
Patent number
US03965100

Reaction notes

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