Hydrochloric Acid → HCID 178524274, compound

HRID 1200028Notes

Reaction equation

HRID 1200028 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[C:7]([C:10]1[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=1)([OH:9])=[O:8].Cl>CN(C)C=O.O>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:17][N:3]=[N:2][N:1]=2)=[N:14][CH:15]=1)([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium Azide2×HCID 27611086-Cyanopyridine-3-carboxylic acid

Product 1

HCID 178524274HCID 178524274, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium azide (12.0 g, 0.18 mol) and anhydrous ammonium chloride (1.5 g) are added to a stirred solution of 5-carboxy-2-cyanopyridine (22.0 g, 0.15 mol) in dry dimethylformamide (375 ml). The reaction mixture is heated to 80° and held at this temperature for 24 h. After this time, a further portion of sodium azide 6.0 g, 0.09 mol) is added and heating continued for a further 24 h. The reaction mixture is then allowed to cool to ambient temperature and diluted with water (560 ml). This solution is acidified to pH 3 with 5N hydrochloric acid and, while a solid precipitates, stirred at this pH for 30 min. The product is filtered off and stirred in refluxing water (60 ml) for 15 min. It is then refiltered, washed with dichloromethane (5×20 ml) and dried in vacuo at 60° to yield the title compound as a light solid; m.p. 257°-259°.

Workup

  1. temperatureThe reaction mixture is heated to 80°
  2. temperatureheating
  3. waitcontinued for a further 24 h
  4. customprecipitates
  5. filtrationThe product is filtered off
  6. stirringstirred
  7. temperaturein refluxing water (60 ml) for 15 min
  8. washwashed with dichloromethane (5×20 ml)
  9. customdried in vacuo at 60°

Sources & evidence

ORD record
ord-054cfd358fa34f8da34ae4b1ff05de45
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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