3-Cyanopyridine → HCID 178420778, compound

HRID 1913375Notes

Reaction equation

HRID 1913375 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[Cl-].[NH4+].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[NH:11]1[C:1]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[N:2][N:13]=[N:12]1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178420778HCID 178420778, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-cyanopyridine (1.1 g, 10.6 mmol) in DMF (15 mL) was added ammonium chloride (718 mg, 13.4 mmol) and sodium azide (824 mg, 12.7 mmol) and the resultant slurry was vigorously stirred at 90° C. for 15 h. The DMF was removed in vacuo, the residue was dissolved in aqueous potassium hydroxide (1 M, 20 mL), washed with EtOAc (2×25 mL), the aqueous layer was adjusted to pH ˜3 with aqueous HCl (6 N) and the solid was collected by filtration to afford the title compound 64 (904 mg, 46% yield) as a white solid: mp=239-241° C. dec.; 1H NMR (CDCl3) δ 9.21 (m, 1H), 8.76 (m, 1H), 8.39 (m, 1H), 7.64 (m, 1H); LRMS (ESI) m/z calcd for C6H6N5 [M+H]+ 148. found 148; HRMS (ESI) m/z calcd for C6H6N5 [M+H]+ 148.0623. found 148.0624; HPLC>99% (tR=4.88 min, 60 (A):40 (B): 0.009 (C); tR=3.74 min, 60 (A):40 (B): 0.02 (C)).

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was dissolved in aqueous potassium hydroxide (1 M, 20 mL)
  3. washwashed with EtOAc (2×25 mL)
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-685d280ec0194239aa07f1df9a80cd98
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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