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HCID 178418361, compound → N-(4-amino-5-methylpyridin-2-yl)acetamide

HRID 537025
Notes
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Reaction equation

HRID 537025 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-])=O)=[CH:4][C:5]([NH:9][C:10](=[O:12])[CH3:11])=[N+:6]([O-])[CH:7]=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:13][C:3]1[C:2]([CH3:1])=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178474345HCID 178474345, compound

Product 1

HCID 66747868N-(4-amino-5-methylpyridin-2-yl)acetamideYield 86.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(5-methyl-4-nitro-1-oxidopyridin-2-yl)acetamide (3.1 g, 14.7 mmol) and Pd(OH)2 (20% on carbon, 1.6 g) in MeOH (80 mL) was allowed to stir under 40 psi of hydrogen at rt for 6 days. The reaction mixture was then filtered over celite and the filter cake was washed with DCM. The filtrate was concentrated to give N-(4-amino-5-methylpyridin-2-yl)acetamide (2.1 g, 86%) which was used without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered over celite
  2. washthe filter cake was washed with DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bc8f879f10754d499ec1db3f0fcd5976
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes