Acetic Acid → HCID 54080160, compound

HRID 918457Notes

Reaction equation

HRID 918457 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:19])=[N:8][C:9]([O:16][CH2:17][CH3:18])=[C:10]([NH2:15])[C:11]=1[NH:12][CH2:13][CH3:14])=[O:5])[CH3:2].C(O)(=O)C.[N:24]([O-])=O.[Na+]>O>[CH2:1]([O:3][C:4]([C:6]1[C:11]2[N:12]([CH2:13][CH3:14])[N:24]=[N:15][C:10]=2[C:9]([O:16][CH2:17][CH3:18])=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 53991223HCID 53991223, compound

Product 1

HCID 54080160HCID 54080160, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26.7 g. of 5-amino-4-ethylamino-6-ethoxy-2-methylpyridine-3-carboxylic acid ethyl ester (0.1 mol.) are dissolved in 100 ml. of acetic acid. At room temperature 7.5 g. of sodium nitrite in 20 ml. of water are added dropwise with continual stirring. The temperature is kept below 20°. The mixture is stirred overnight and then evaporated to dryness. 100 ml. of water are added to the residue which is then extracted three times with 50 ml. portions of ether. The organic layer is collected, dried over sodium sulfate, filtered and the solvent distilled off. The residue of 4-ethoxy-1-ethyl-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine-7-carboxylic acid ethyl ester is recrystallized from ligroin, yield 75%, m.p. 56°-58°.

Workup

  1. customAt room temperature
  2. customis kept below 20°
  3. customevaporated to dryness
  4. additionof water are added to the residue which
  5. extractionis then extracted three times with 50 ml
  6. customThe organic layer is collected
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. distillationthe solvent distilled off
  10. customThe residue of 4-ethoxy-1-ethyl-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine-7-carboxylic acid ethyl ester is recrystallized from ligroin, yield 75%, m.p. 56°-58°

Sources & evidence

ORD record
ord-00f54875ac614c3582a49e2ad9d2cc9d
Source dataset
uspto-grants-1976_07
Patent number
US03971800

Reaction notes

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