Acetonitrile → HCID 178419382, compound

HRID 66019Notes

Reaction equation

HRID 66019 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(#N)C.[Br:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)C>[Br-:13].[CH2:14]([C:1]1[NH+:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 274090Imidazo(1,5-a)pyridine

Product 1

HCID 178419382HCID 178419382, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Imidazo[1,5-a]pyridine (3.9 g.) in 100 ml. of dry acetonitrile is treated with 6.8 g. of α-bromotoluene, and the resulting reaction mixture heated under reflux for 3 hrs. The solution is cooled and diluted with 250 ml. of diethyl ether. The resulting precipitate is filtered and recrystallized from isopropanol-diethyl ether, 7.92 g., m.p. 172-176° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hrs
  3. temperatureThe solution is cooled
  4. additiondiluted with 250 ml
  5. filtrationThe resulting precipitate is filtered
  6. customrecrystallized from isopropanol-diethyl ether, 7.92 g

Sources & evidence

ORD record
ord-52b39dafd60e443fa79424fe2b0238b5
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Reaction notes

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