Hydrochloric Acid → HCID 178497262, compound

HRID 1096960Notes

Reaction equation

HRID 1096960 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[C:13]([C:15]1[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:18]=[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:16]=1)#[N:14].Cl>CN(C=O)C>[C:25]1([C:17]2[CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=[C:15]([C:13]3[NH:14][N:3]=[N:2][N:1]=3)[N:16]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 57930992Methyl 2-cyano-6-phenylisonicotinate

Product 1

HCID 178497262HCID 178497262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (1.7 g) and triethylamine hydrochloride (3.5 g) were added to a DMF (80 mL) solution of methyl 2-cyano-6-phenylpyridine-4-carboxylate (2 g), and stirred overnight at 100° C. With cooling with ice, diluted hydrochloric acid was added to it, and extracted with a mixed solution of chloroform/methanol=10/1. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away to obtain the title compound as a brown solid.

Workup

  1. additionwas added to it
  2. extractionextracted with a mixed solution of chloroform/methanol=10/1
  3. washThe organic layer was washed with water and saturated saline water
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-28b61532d17a4f34a81089fd503a623f
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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