Sodium Hydroxide → 2-(1H-1,2,4-Triazol-1-yl)pyridin-3-amine

HRID 979408Notes

Reaction equation

HRID 979408 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[OH-].[Na+]>Cl>[NH2:1][C:4]1[C:5]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13911193HCID 13911193, compound

Product 1

HCID 139111942-(1H-1,2,4-Triazol-1-yl)pyridin-3-amineYield 35.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension containing 35.4 g of stannous chloride dihydrate in 100 ml of concentrated hydrochloric acid was added portionwise 10 g of the compound prepared in Example 1 over a 0.25 hour period. After the resulting exotherm (23°-79°) slowed, the suspension was heated at 85°-90° for one hour, then cooled to 0°. The mixture was poured onto excess ice-water (about 700 ml), and the suspension was made strongly basic to litmus by addition of 50% aqueous NaOH to yield a precipitate. After filtering the mixture, the isolated solid was washed with water, suction-dried, then recrystallized from ethyl acetate-hexanes to yield 3 g of the subject compound; m.p. 103°-105°.

Workup

  1. customAfter the resulting exotherm (23°-79°)
  2. temperaturethe suspension was heated at 85°-90° for one hour
  3. temperaturecooled to 0°
  4. customto yield a precipitate
  5. filtrationAfter filtering the mixture
  6. washthe isolated solid was washed with water
  7. customsuction-dried
  8. customrecrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-81de04867ba04069822bc34d78662bea
Source dataset
uspto-grants-1987_05
Patent number
US04668279

Reaction notes

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