Sodium Azide → 2-Azidomethyl-5-propoxy-pyridin-4-ol

HRID 2236539Notes

Reaction equation

HRID 2236539 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]1[CH:12]=[C:11]([OH:13])[C:10]([O:14][CH2:15][CH2:16][CH3:17])=[CH:9][N:8]=1>CN(C)C=O>[N:1]([CH2:6][C:7]1[CH:12]=[C:11]([OH:13])[C:10]([O:14][CH2:15][CH2:16][CH3:17])=[CH:9][N:8]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178458779HCID 178458779, compound

Product 1

HCID 1784587892-Azidomethyl-5-propoxy-pyridin-4-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium azide (2.82 g, 43.3 mmole) in 30 mL of N,N-dimethylformamide is added 2-chloromethyl-5-propoxy-pyridin-4-ol (8.74 g, 43.3 mmole). This is stirred for overnight at ambient temperature then quenched into ice water. The solid formed is filtered, washed with cold water and dried to give an off white solid, 5.74 g, (63%); MS (ES+): m/z 209.3 (M+H).

Workup

  1. customthen quenched into ice water
  2. customThe solid formed
  3. filtrationis filtered
  4. washwashed with cold water
  5. customdried
  6. customto give an off white solid, 5.74 g, (63%)

Sources & evidence

ORD record
ord-67ed3b4eb1544676b1725ced3ff6a336
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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