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

HRID 81488Notes

Reaction equation

HRID 81488 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-3147b6d8ef0a4ebe9c6078be1d95b6ee
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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