Sodium Azide → HCID 86038331, compound

HRID 2233893Notes

Reaction equation

HRID 2233893 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[N+:8]=1[O-:9].N([O-])=O.[Na+].[N-:18]=[N+:19]=[N-].[Na+]>Cl>[N:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[N+:8]=1[O-:9])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 178497950HCID 178497950, compound2×

Product 1

HCID 86038331HCID 86038331, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

Methyl 6-aminopyridine-2-carboxylate 1-oxide hydrochloride (Intermediate 122, 3.34 g, 16 mmol) was dissolved in 10% HCl (aqueous) and cooled to 5° C. An aqueous solution of NaNO2 (1.5 g, 21 mmol) was added dropwise maintaining temperature below 5° C. After 15 minutes of stirring, an aqueous solution of NaN3 (1.4 g, 21 mmol) was added dropwise maintaining temperature below 5° C. The reaction was stirred at 5° C. for 30 minutes and slowly warmed to room temperature. The product was extracted with DCM and then the aqueous layer was basified (with 50% NaOH to pH 13) and then extracted again with DCM. Drying (MgSO4) and removal of solvent yielded a yellow oil (2.6 g, 82%).

Workup

  1. temperaturemaintaining temperature below 5° C
  2. temperaturemaintaining temperature below 5° C
  3. stirringThe reaction was stirred at 5° C. for 30 minutes
  4. temperatureslowly warmed to room temperature
  5. extractionThe product was extracted with DCM
  6. extractionextracted again with DCM
  7. customDrying
  8. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-4939618fc0ff4a3ca84dcc65be8724c3
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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