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Ethyl orthoformate → ethyl [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

HRID 1502104
Notes
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Reaction equation

HRID 1502104 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:6]=[N:7][C:2]([N:1]2[CH:14]=[N:26][N:25]=[N:24]2)=[CH:3][CH:4]=1)[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 67143734Ethyl 2-(6-aminopyridin-3-yl)acetate

Product 1

HCID 77230693ethyl [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of ethyl (6-aminopyridin-3-yl)acetate (0.55 g, 3.05 mmol), CH(OEt)3 (1.35 g, 9.15 mmol) in AcOH (20 mL) was added NaN3 (0.24 g, 3.7 mmol) at room temperature. The mixture was heated to 80° C. and stirred for 3 hours. The mixture was concentrated under reduce pressure. Water was added, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography via silica gel to give ethyl[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate.

Workup

  1. concentrationThe mixture was concentrated
  2. additionWater was added
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography via silica gel

Sources & evidence

ORD record
ord-b3373f1aaba447c1ae4ed6c68527e56f
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206199B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes