Acetic Acid → HCID 89543726, compound

HRID 2281299Notes

Reaction equation

HRID 2281299 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(O)(=O)C.[CH:16](OCC)(OCC)OCC.[N-:26]=[N+:27]=[N-:28].[Na+]>O>[N:1]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH:16]=[N:28][N:27]=[N:26]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 1514432Methyl 5-aminopyridine-3-carboxylate

Product 1

HCID 89543726HCID 89543726, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 5-aminonicotinate (5.0 g, 33 mmol) in acetic acid (47 ml, 820 mmol) was treated with triethyl orthoformate (8.8 ml, 53 mmol), followed by sodium azide (3.2 g, 49 mmol). The resulting mixture was heated at 80° C. for 1 hour, after which the reaction mixture was cooled to room temperature and diluted with water. The resulting precipitate was collected and dried under high vacuum to provide methyl 5-(1H-tetrazol-1-yl)nicotinate.

Workup

  1. temperatureafter which the reaction mixture was cooled to room temperature
  2. customThe resulting precipitate was collected
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-c8fada8c03f7418fb8da240ec187f0fa
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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