Benzonitrile → HCID 50915484, compound

HRID 517648Notes

Reaction equation

HRID 517648 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu]Cl>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=[C:2]2[CH:7]=1

Participants

5

Reactant 3

HCID 7505BenzonitrileHCID 212261,10-Phenanthroline hydrateHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 50915484HCID 50915484, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-4-chloropyridine (5.00 g, 38.9 mmol), copper (I) chloride (195 mg, 1.97 mmol), 1,10-phenanthroline monohydrate (390 mg, 1.97 mmol) and benzonitrile (65 mL) was heated in a 100 mL 4-necked flask to 130° C. During 23 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below). The dark brown suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (50 mL) and dried to yield crude 7-chloro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (7.09 g, 79%) as a green solid with 100% purity (HPLC area-%, method see below).

Workup

  1. customDuring 23 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below)
  2. temperatureThe dark brown suspension was then cooled to 0-5° C.
  3. filtrationfiltered
  4. washThe filter cake was washed with TBME (50 mL)
  5. customdried

Sources & evidence

ORD record
ord-e29ea3f70347494db65d98ce0327e577
Source dataset
uspto-grants-2015_08
Patent number
US09115130B2

Reaction notes

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