Sodium Hydroxide → 6-(1-Aminoethyl)-3-(4-methylbenzyl)-1,2,4-triazin-5(4H)-one

HRID 890692Notes

Reaction equation

HRID 890692 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[NH:12][C:11](=[O:13])[C:10]([CH:14]([NH:16]C(=O)C)[CH3:15])=[N:9][N:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>Cl>[NH2:16][CH:14]([C:10]1[C:11](=[O:13])[NH:12][C:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([CH3:1])=[CH:3][CH:4]=2)=[N:8][N:9]=1)[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135697912N-{1-[3-(4-Methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

Product 1

HCID 1356979156-(1-Aminoethyl)-3-(4-methylbenzyl)-1,2,4-triazin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

20 g (69.9 mmol) of N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide (Example 7A) are stirred under reflux in 200 ml of 2 N hydrochloric acid for 18 h. The cooled mixture is then neutralized using 6 N NaOH and evaporated to dryness in vacuo. The residue is suspended in methanol and the salt is separated off. The concentrated filtrate is flash-chromatographed using dichloromethane/methanol 20/1 and 5/1.

Workup

  1. customevaporated to dryness in vacuo
  2. customthe salt is separated off
  3. customThe concentrated filtrate is flash-chromatographed

Sources & evidence

ORD record
ord-d6faca53fd5740f1a2dc49f3e041c634
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

Loading…