Ammonium Chloride → HCID 59754786, compound

HRID 751433Notes

Reaction equation

HRID 751433 reaction equation
[Na].[CH:2]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)=O.[CH2:12]([O:14][C:15](=[O:20])[CH2:16][N:17]=[N+:18]=[N-:19])[CH3:13].[NH4+].[Cl-]>CCO>[N:17](/[C:16](=[CH:2]\[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)/[C:15]([O:14][CH2:12][CH3:13])=[O:20])=[N+:18]=[N-:19]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545SodiumHCID 109755495-Methoxy-3-pyridinecarboxaldehyde

Product 1

HCID 59754786HCID 59754786, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-15 °C

Procedure

To a cooled (−15° C.) solution of anhydrous EtOH (270 mL) was added sodium metal (4.46 g, 0.194 mol) slowly. After complete reaction a mixture of 3-formyl-5-methoxypyridine (7.5 g, 54.7 mmol) and ethylazidoacetate (25.0 g, 0.194 mol) was added so as to maintain an internal temperature of −15° C. The reaction mixture was kept at −15° C. for 72 hours after which it was poured into a 30% aq. NH4Cl solution, extracted with EtOAc (2×250 mL), the organic phase dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on silica gel eluting with a gradient of 0 to 35% EtOAc in hexanes to afford the title compound.

Workup

  1. customAfter complete reaction
  2. additionwas added so as
  3. extractionextracted with EtOAc (2×250 mL)
  4. dry with materialthe organic phase dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on silica gel eluting with a gradient of 0 to 35% EtOAc in hexanes

Sources & evidence

ORD record
ord-4982af0292d140d6a58c0851a44444ba
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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