Sodium Hydroxide → (2-Amino-pyridin-3-yl)-pyridin-3-yl-methanone

HRID 2387218Notes

Reaction equation

HRID 2387218 reaction equation
CC(C)(C)C([NH:5][C:6]1[C:11]([C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)=O.[OH-].[Na+]>Cl>[NH2:5][C:6]1[C:11]([C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686311822,2-dimethyl-N-[3-(pyridine-3-carbonyl)-pyridin-2-yl]-propionamide

Product 1

HCID 53678495(2-Amino-pyridin-3-yl)-pyridin-3-yl-methanone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2,2-dimethyl-N-[3-(pyridine-3-carbonyl)-pyridin-2-yl]-propionamide (0.225 g, 0.79 mmol) in 3M HCl (10 ml) is heated at reflux for 4 hours. The reaction mixture is allowed to cool to room temperature and the pH adjusted to basic with 2M NaOH. The product is extracted into DCM, dried (MgSO4), and concentrated in vacuo to afford a yellow solid. Drying in vacuo at 45° C. overnight yields (2-Amino-pyridin-3-yl)-pyridin-3-yl-methanone [M+H]+ 200.

Workup

  1. temperatureat reflux for 4 hours
  2. extractionThe product is extracted into DCM
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a yellow solid
  6. customDrying in vacuo at 45° C. overnight

Sources & evidence

ORD record
ord-b983abd0394942b4b4ccfceb8f6ac094
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Reaction notes

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