6-Methyl-5-nitropyridin-2-amine → HCID 178433443, compound

HRID 363321

Reaction equation

HRID 363321 reaction equation
N[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.N([O-])=[O:13].[Na+]>O>[OH:13][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2479766-Methyl-5-nitropyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 178433443HCID 178433443, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 3.0 gm (19.6 mMol) 6-amino-3-nitro-2-picoline in 50 mL water containing 3.5 mL concentrated sulfuric acid was heated to effect solution. The resultant solution was cooled to 0° C. and a solution of 2.0 gm (29.4 mMol) sodium nitrite in 10 mL water was added with vigorous stirring at a rate to maintain the reaction mixture ≤10° C. After 4 hours the reaction mixture was filtered. The solid was washed with water and dried under reduced pressure to provide 2.4 gm (80%) of the desired compound as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto maintain the reaction mixture ≤10° C
  3. filtrationAfter 4 hours the reaction mixture was filtered
  4. washThe solid was washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-9d92017cd9a543b2af904d7ec9737b75
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Linked notes

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